Thanks, Tober, and good morning, everyone. Welcome to Frontier. Thirteen years ago, I started Addigy because I believed Apple devices deserved a management platform built for how your organization actually works. Live, connected, always reachable, real time. Today, that decision stops being an architecture choice. It becomes the foundation of Addigy’s frontier. And here’s the job as I see it. Your Apple fleet should do three things: make your people productive, safeguard them as they work, and unlock more of what those devices can actually do. If we do our job right, you get the confidence and the foundational capabilities to make your whole organization more effective. That’s the bar for everything you’ll see today. So let’s get into it, the frontier of Apple fleet management. If you remember one sentence from the next thirty minutes, make it this one. Real time is the precondition for autonomous operation, and Addigy is the only Apple platform built on it. An agent is only as good as what it can see, how fast it can act, and the guardrails your vendor helps you keep around it. AI agents are highly capable, and that same capability makes them a risk you have to manage. If your platform learns about a device’s state on a fifteen minute check-in cycle and there’s well known MDM platforms running on eight hour check-in cycles, your agent is reasoning about the past, acting on old or even inaccurate information. You’ll start to see why that matters in the current threat landscape. AI has changed the speed and scale of attacks. Vulnerabilities are weaponized in hours, and campaigns run at machine speed. Gartner’s endpoint security analysts, Eric Reiner and Chris Silva, have made the point that your endpoint management platform is your first line of defense, the most proactive layer you have, and it can only defend at the speed it can execute. This autonomous operation requires what I call a live nervous system: current state in, immediate action out. When the attack moves at machine speed, a fifteen minute check-in cycle is effectively an unlocked door. Running that nervous system costs real money. Persistent connections to every device all the time is infrastructure most vendors chose not to pay for. We’ve carried that investment in Experience for You since two thousand fourteen, and it pays off for admins and for end users alike. And it lets your fleet work at the speed of your organization. Everything you see today is the consequence of that one decision. Now let’s talk about why focus matters, especially now. Apple continues to raise the bar for device management vendors. Most are not keeping up, and Apple is quickly rendering those legacy vendors literally obsolete. Start with declarative device management First, understand what legacy MDM actually was. You threw a command over Apple’s wall and hoped it landed. No confirmation. No receipt. Most MDMs just threw it over and their organizations ran on hope. That is exactly why we built a persistent real time agent. It was the only way to verify a change actually happened on the machine. Declared device management flips this model. You declare the desired state, and the device itself enforces it. Now that’s real progress, and Apple has made it the required infrastructure going forward, deprecating legacy commands with a clock counting down to obsolescence. But no protocol executes with one hundred percent precision, and you cannot build a fleet on the assumption that this one will. So with Addigy, declare device management sets the state and the Realtime Agent independently verifies on the endpoint itself, that the change landed and that it holds. Auditable at any moment. You’re not running on hope, and you’re not placing blind trust in a single protocol. No other vendor runs both mechanisms. Then there’s the cadence. Apple ships a major OS every fall. Rapid security releases in between, and your management vendor is expected to support them the day they land. Apple Business Manager and User Enrollment, Apple’s rails for owning corporate devices and separating work identity from personal. Keep reshaping how identity works on the platform. And there’s Apple Silicon. Change what enterprise fleet even looks like. It’s group policy, WSUS Active Directory being reinvented at once on a yearly cadence by a vendor that doesn’t wait for anyone. All this is evolving technology, and we are constantly moving things under the hood to track it. File vault management started on the command line. Once the MDM path was robust enough, we moved it to MDM only. OS patching followed that same arc. Through every transition, we’ve kept you on the most robust layer available while adopting Apple’s latest and feeding back to Apple until it’s reliable as it can be. When your vendor does this right, you never have to think about the intricacies. That’s our job. Now compare Focus to the do it all UEM tools. For them, Apple is a secondary road map. New Apple protocols land late, and that’s if they land at all. No real time state. Focus is what our customers deserve, and it runs deeper than the platform. It’s the new technology made robust before you rely on it. Declare device management with the verifiable layer underneath and its Apple expertise in every person you touch at Addigy, sales, success, support, technology, the people behind it, and the passion for your success. Now this slide is the whole argument in one image. MDM, even declared device management, is the base layer infrastructure. It configures the device, and that’s where its job ends. Everything your organization actually needs sits in the layer above it. The floor is the transformation every fleet is being forced through right now. Legacy conventional MDM is going away, and everything is moving to declarative MDM. Addigy leads all vendors in support of declarative MDM. Just ask Apple. If your platform hasn’t made that move for you, you’re months away from major risks. We even go a step further. As soon as Apple releases a new declarative payload, it is fully supported in Addigy through our APIs the same day, with this autonomous process full QA tested before availability in our API. The layer above it is the one that changes everything. Real time agent management and scripting, live agent, a command line automation on every device. This layer is the mechanism that makes every layer above it live instead of queued and hence delayed. On top of that, always on compliance and conditional access. And compliance is its own moving target now. CIS, NIST, DISA, CMC, Cyber Essentials in Europe. The benchmark list keeps growing, and AI compliance standards are joining it, with more on the way. We enforce them continuously as policy with live posture and access gated on it, so a new benchmark is a checkbox for you, not a project. Then ShadowAI monitoring and management, discovery of AI usage, dynamic AIDNS, egress governance, and at the top, the security suite with declarative OS and CV patching. Now look at the bracket on the right: the speed of live. Notice what’s inside the bracket and what isn’t. Conventional MDM sits outside it. In an environment where attack windows are measured in hours and fleets are measured in thousands, speed of operation is the utility everything else is built on. No delays because you have real time execution. So what do we do with all this speed? Three things, and they are compounded. Identity, and this is where your end user’s digital experience starts. Onboarding is not installing software onto a device. It’s guiding a person from the first power on, they sign in with their company identity, and everything springs up specific to them: their apps, their access, their settings. The abstraction layer is the user, not the device. Underneath it, the platform SSO broker proves the user is legit with an identity provider, pass keys live in the secure enclave, And phishing resistant MFA is the default, not the upgrade. Resiliency. The fleet stays healthy and recovers on its own. Declarative OS patching, automated CVE patching, auto remediation, and real time state underneath all of it. Lastly, security: enforce and defend EDR twenty fourseven MDR, Managed Detection Response, CISNISTAS policy not as an audit weak scramble, conditional access decisions made on live posture and shadow AI governed with Fable DNS, whether you want to outright block usage or simply monitor it. Each one is valuable alone. Together they compound into one outcome: verified users on healthy devices defended in real time. That’s Zero Trust as a result you can observe. Now the reason you’re really here. For the last year, the industry has been chasing one problem: AI is discovering vulnerabilities faster than humans can patch them. The window between disclosure and exploitation keeps shrinking. The bottleneck isn’t detection anymore. The bottleneck is everything after detection. So we built the bridge, all four spans of it. Detect. CV detection maps exposure across every device in the fleet in real time. Mitigate. While a patch is pending, customized compliance utilities lock down the exposed device. You’re protected before the patch exists. Automated CV patching across third party apps and the OS, delivered declaratively, riding Apple’s own declarative rails. Verify, and this is the part I’m proudest of. Patch efficacy is judged across the fleet. The fleet’s own telemetry makes the promote or hold call. No single admin staring at one test machine making a judgment call for ten thousand devices. The team will walk you through the release schedule of beta and GA and what lands through the end of the year in the sessions ahead. Let’s zoom in to security and the timeline for security events. Everything on the left of this slide is proactive: configuration and compliance enforced continuously, shadow AI governed with dynamic AIDNS. Devices are locked down the moment a CV is disclosed. Automated patching, landing before exploitation. Every one of those moves happens left of boom, before the incident. Then there’s the boom. Because sometimes, despite everything, boom happens. Everything on the right is what responds, Send to one EDR and MDR, twenty four by seven, SIM analysis. And further right, the part nobody puts on a slide, postmortems and cyber insurance claims. Every dollar and every weekend your team spends on the right side is a dollar in a weekend the left side could have hopefully saved. Addigy keeps to work left of Boom, and when Boom happens anyway, the security suite is already on the device protecting it. Now let’s zoom out to the full AI layer because patching is one door into it. Six capabilities, one map. MCP access is the major interface right now for AI. The full MDM control pane exposed over MCP, with admin set guardrails on every agent action AI monitoring visibility into AI usage across the fleet which tools, which models, which devices AI compliance AI standards enforced as a policy right alongside CIS and NIST Our AI script helper, natural language to production safe scripts inside the console. AI report builder, ask the report in plain language, built for teams not yet running MCP. And Fable DNS, dynamic AI DNS, shadow AI discovery, and the agentic egress governance at the network layer. Notice the tags: Observe and Orchestrate. Every capability is available through both lenses. If your team is agent forward, the whole platform is addressable over MCP. If your team isn’t there yet, the console gives you the same power in plain language. One AI layer, two doors in. Our job isn’t to force anyone through a door. It’s to help you adapt and rise to the AI era of Apple at work from wherever you’re starting. One more launched JSON story because identity is where the end user actually feels your platform. Platform SSO is Apple’s right answer for modern authentication on the Mac. But PurityP implementations have been fragmented and honestly broken for arguably four years. Different flows, different failure modes, different security postures depending on which IDP you bought. We now have a broker that ends this. Direct Platform SSO on Apple’s native framework brokered to your IDP, not reliant on how or if your IDP implemented platform SSO. One consistent experience. The same flow whether you run Google, Microsoft Okta, or any SAML IDP. Easier for the end user, easier for the admin, and uniformly secure. No per IDP implementation disparity. One hardened path for every provider. This has never been done before by any MDM vendor. We are not waiting any longer for IDPs to implement it right. We are taking ownership and doing it right for you. This is also the moment Mac finally speaks the language most admins were trained in, managing by users with a truly native company login carried through single sign on across the applications on the device. Now is all of this real engineering or an AI story stapled onto a road map? Let me show you how we built. We call it moving left, pushing the quality decisions to the earliest possible moment, where they’re cheapest to make and the hardest to fake. It starts with our signaling dashboard, which is really us listening to you. Every support ticket, every call with your account manager, every signal from the fleet gets pulled together into data that decides what we work on. Evidence outranks opinion, including mine. Those signals feed the concept agent: proofs of concept built before we’re invested, stripping out our own biases, pressure testing a capability from every angle, aligned to your outcomes rather than to our assumptions. The concept then becomes the PRD, the product requirement document, and that document is the source of truth for everything downstream. It’s the record of what we said we would build, and it’s what the QA agent validates every build against. If the product drifts from the promise, QA catches it. AI authors at every stage, humans judge at every gate, nothing ships on vibes. And here’s the proof: zero point three two percent change failure rate, which is elite in engineering, and thirty five percent plus speed to market against a ten percent target. Read those two numbers together because the order matters. Moving left is the whole strategy. Better signals choose the right products. Better design builds them right. And better QA proves it. In an industry drowning in AI slop, we made quality the constraint, and speed showed up anyway. The trust we engineer internally is the product we ship externally. Which brings me to the most important slide of the day, and it has the fewest words on it. What does trust mean to us? Autonomy works inside your guardrails. You set them. We enforce them. The goal is real autonomous work. A vulnerability patched across the fleet without a human driving every step. You define the guardrails and the intent. The platform brings the fleet data and the execution. And the combination makes better autonomous decisions than either side alone. Autonomy you can’t govern isn’t autonomy. It’s a liability, maybe with good marketing. The MCP control plane and the Addigy Assist agentic layer coming with it are built to keep raising that bar. Every capability we expose through it ships with guardrails designed in. So however you operate through AI, it stays within the fundamental working rules of IT. Trust here isn’t a setting. It’s something we keep shaping release after release. And trust extends to your data. We are not sending any of your data to frontier models. Not under the enterprise license, not at a no training clause, not at all. Everything in our product is processed locally, protected locally inside our environment. Trust is a partnership with your vendor, and this is our side of it. Every step of the frontier runs inside this trust model. That’s a commitment on the record on this stage. So here’s where we are. Real time is the precondition for autonomous operation, and Addigy is the only Apple platform built on it. You saw the stack, bottom and top, and the bridge from CV disclosure to fleet verified patch. The platform is half of it. The other half is a commitment Apple expertise in the product and the partnership, doing the toil you never have to see. The under the hood migrations, the benchmark churn, the verification of every endpoint. All of it so the outcomes are what you are actually feeling. Your people are more productive on the devices they love, protected by the best security we know how to build, and the job of running all of it simpler every year through our trusted partnership with you.
The Frontier of Apple Fleet Management
Agentic Apple management is here
See how Addigy is building for what Apple actually ships, from DDM to AI-era security expectations.
Speaker: Jason Dettbarn, CTO & Founder, Addigy
Good morning, and welcome to Addigy Frontier. Thank you, Jason, for that wonderful keynote. And I’m super excited to come now to our Apple security panel. This title, 84% of businesses run Macs, so do a 100% of attackers. Well, we’ll get right into it. But I’m super excited to be spending some more time with Patrick Wordle and Matt Lee of PAX eight. But myself, Angela Diico here, product marketing manager at Addigy, and I’m really just trying to get the the conversation started over here. But I will talk a little bit more to… Well, I’ll let the two of you gentlemen introduce yourselves more. So I know Patrick, CEO of W and doing some really great work with your project Objective C and and getting the next sort of generation of IT admins up to speed here and ready to tackle these problems. But I’ll I’ll I’ll let you kinda take it away here, Patrick. Angela, thank you. And, also, thank you to Addigy. Very stoked to talk super nerdy about all things related to Apple security. Yeah. As Angela mentioned, I really, for better or worse, live and breathe Apple security about twenty years now, largely diving into threats, exploit malware that’s targeting Apple’s, probably desktop, but also mobile operating systems. So, again, very excited to be here and, hand it off to Matt now to introduce himself as well. Yeah. Thanks, Patrick. I’m I’m excited. I’m the dumb guy in the room today. This is fantastic, so this works well. Yeah. Matt Lee. I have been in the managed service community, managed service provider community since about 2011. Prior to that in a whole different… Bunch of different organizations. But I’m super excited today to bring what I work on, is the operations side, the tactical delivery of security at the end for managed service providers, and ultimately those that support the small to mid sized business and serve that 43% of the GDP that lives below what Wendy Nathor coins the cybersecurity poverty line. So thanks for having me here. I’m excited to talk about frameworks and operations and and Mac security. Very cool. Awesome. Alright. So without further ado, so we’ll get right into it with where this stat came from. And what I’m I’m hoping for us to do here is dive in a little bit more, Patrick, to your research. Matt, the lot of the really interesting frameworks that you have and the work that you’ve been doing with Pax8 and also your own companies and initiatives to kinda give people a view, you know, whether you’re an MSP, you’re an IT director, you’re an IT leader. Just some kind of like new new ways and new lenses to kind of use when we’re talking about security in Apple. But, yeah, where where did this stat come from, Patrick? I’ll I’ll leave that over to you. Sure. So I guess I’m gonna somewhat date myself. But, yeah, maybe about fifteen, maybe twenty years ago when I started Mac security research, Mac was really just this second, third class citizen. Like, even when I was at the National Security Agency, none of our targets were running Mac. And so, like, nobody really cared. And maybe it’s a little of a harsh statement, but since then, Macs have just proliferated. I think many of us dearly love our MacBooks, our Mac Minis, our Apple products, and I think business in the enterprise has equally embraced Macs. You know, this statistic is, you know, almost 85 of of businesses run Macs. And so the follow-up kind of play on this is that means that, essentially, all attackers who are, almost by definition, very opportunistic, are starting to focus on macOS as well. And we’ve seen this not just anecdotally. I think the data backs us up as well. Each year, I really dive into all the new Mac malware samples. And over the last few years, many of these variants, these malware has actually existed on other platform before on Windows and Linux. And so as Mac, though, has become more prolific in the enterprise, what we are seeing is the attackers porting their existing threats, also building new ones, but porting a lot of times their existing Windows and Linux malware to to Mac OS. And, you know, there’s a lot of debate why as Macs become more popular, so does Mac malware. To me, it’s super simple. And, again, it just comes down to the fact that attackers are super opportunistic. And as Mac increases in terms of its market share and prevalence in, especially, enterprise, it’s really a no brainer for attackers to follow suit. So I don’t know if Matt can give something to add to that as well or… I do. I’ll add. You know, Willie Sutton in the nineteen forties or so is going to have said, why do you rob banks? He said, well, because that’s where the money is, stupid. Right? And so, like, I think there’s an element of of saying that more and more… I’m sitting in front of five Macs I’ve purchased in the last year. Right? So, like, like the more and more people are adopting Macs and maybe shelving away their Linux and certainly in the enterprise world, Windows. As we’ve gone more identity centric, meaning I has OAuth token and can access OAuth apps, it doesn’t matter where the device is and what device it is. And so people have tended to go towards MACs, and that means threat actors have now shifted their focus to where they’re gonna get the token and be able to have access to things. So It’s where the money is. That’s right. As Willie Sutton so perfectly said. Very prophetic. Yeah. No. But this is great. I mean, well, it’s not great, but it leads into really this idea that we started talking about that Jason was really kind of, you know, touched on a bit in the keynote about, you know, like, who who can you trust? So knowing, you know, that we’re we’re kind of dealing with a whole new landscape out here, you know, what… How can we, you know, kind of take a new lens to think about, you know, how do we talk to our vendors? What tools do we want to be able to use? Like, what’s our process to vet those folks? So this is really kind of I think the through line, but this idea of, you know, like security is operations. I know Matt, you and I really talked about this, and this is this is gonna be a big part of the discussion. So hopefully, we’ll be able to walk away here with again more of those takeaways, but Max being the target now. You know? Like I just… I do wanna set the stage of securities operations. Right? And and I’ll make another hyperbolus analogy for this for this point. But if you are in the Simpsons metaverse and you’re gonna go to a doctor, is it doctor Nick? Like, does does doctor Nick need to be the guy cutting on you because hi, everybody, was not a very good doctor, actually. Right? And and my point is, like, you can have the best scalpels and the fat spreaders and the lights and the most sanitary rooms, but if I’m the guy wheeling the scalpel, you’re in really bad shape. I have slept in a Holiday Inn Express, but that does not make me a surgeon. And so the challenges that we like to think of as, oh, I’ll just buy another tool and we’re going to get into this in a bit. But it really is if you can’t operate upon those and you can’t do things and take action upon it, not gonna do the things that are necessary to reduce the impact in the blast radius in an environment when something does happen. Right? Oh, that Mac has a problem. I’m gonna isolate that. I’m gonna deal with those user accounts. I’m gonna deal with the identities. Those are responses that take operational things to be able to drive forward. And and if we think about this in a more simpler… More simple term, because simpler is not a word, when you look at NIST, it’s identify, protect, then detect, respond, and recover. And and detect, respond, and recover are all after the boom happens. Right? And and and it’s all after something kinetic has happened, a piece of malware that Patrick has studied, has landed on your machine, has executed, has bypassed EDR, now we’re doing something in that in that path. That takes operations to be able to reduce that blast radius ex post facto. So my take is that so many people like to think the tools get you there. Buying a gym membership gets me fit. Negative. Going to the gym does and eating better and those things that are corollary to that in operations. Alright. But that’s my thoughts is people need to stop saying, I can buy a tool. When you think, what are those operational aspects that need to support this that can take a strategy, take it into its tactics, and then break it down into operations, and execute upon those operations? A 100%. No. And that’s a really great great point. And what is perfect actually thing now for us to talk about is this idea of, okay. Like, so what are we dealing with? Like, what’s the shifts that we’re seeing and what… If you could, Patrick, talk a little bit about this, because I know you you have such a a breadth of really, like, deep in the weeds of research to bring to folks here. I mean, if you could, you know, just kinda walk us through some of that. Like, what what should folks know going into, you know, managing their Macs and managing their Apple devices? Yeah. So there’s there’s a few things. One, I really appreciate what Apple has done natively at the operating system level. So we already touched on the fact that Macs are becoming more popular. I think this is a trend that’s gonna increase. There’s predictions that in the next few years, the… There’s an inflection point where the number of Mac machines is gonna overtake Windows. Whether or not you think that’s gonna happen in next year, next few years, I think we all agree that’s probably eventually gonna happen. So as we mentioned earlier, the attackers are watching that too, going after that increased market share. Now the good news is Apple, I think, has done a really good job. And on the previous slide, it was like, okay. Who do you trust? And, you know, one thing I really like about Apple is they’re super privacy centric. They make their money largely when they sell you the hardware or an App Store commissions, but that’s a separate thing. So the good news is they’re… An operating system that’s built largely on privacy is is generally pretty secure as well. So for example, you know, process a cannot read the the memory of of process b. That’s for privacy reasons, but that’s super beneficial because that also means if malware infects your system, it can’t easily, without some exploit or very sophisticated capabilities, inject, for example, into your browser or into your key chain to steal tokens. So the the lucky thing is I think Apple has done a really good job building a very solid baseline that hackers and and adversaries are wily creative. And so, you know, I think what we’re seeing is, for better or worse, it’s always gonna be a a cat and mouse game. And so Apple increases the sophistication of the native security as Mac users become a little bit more educated about the threats. You know, what we’re seeing is the adversaries are somewhat in lockstep becoming more sophisticated. So, yes, some of the Mac attacks are still pretty basic. I think there are some gaps where Mac users might need to be a little bit more aware of what’s happening in terms of the fact that, yes, they are being targeted sometimes by very sophisticated adversaries. And the operating system, while it will do a really good job, is not necessarily enough. So for example, many people don’t know that built into Mac OS is a rudimentary antivirus system. It uses signatures, and it attempts to detect and block no malware. Now Apple doesn’t really talk a lot about that, which I think is a little less than ideal, because I think security through obscurity is never a good thing. I’m a big proponent of being super transparent. And so, for example, now it’s a little bit improved. But when Apple kinda rolled this out, they didn’t even really chat about it. And if that system detected and blocked that, there was no alert that could be sent, for example, to a SIM or a Mac admin to say, oh, you know, there was an attack, but the core component of the operating system blocked that, which is is a very important thing to know because if the operating system didn’t block it, you have, as Matt said, many other steps that you should take. Whereas if it did, k, you might be in the clear. So there’s definitely some things that built into the operating system. We don’t, I would say, have enough transparency or insights. And to kind of go along a little bit further with that, I think Apple sometimes has made the constant… Conscious decision that security, in many cases, they’re gonna kinda delegate that out to third party tool inning. The Mac admins, the IT teams, they really design an operating system that’s very privacy and security centric, but by design, doesn’t do everything. So we see adversaries sometimes implementing attacks. You know, click fix is one recent one where they get the users to copy and paste something. Initially, the operating system kind of just allowed that. The reason adversaries went that route is running stuff from the terminal, really sidesteps a lot of Apple’s built in capabilities. Apple recently introduced the mechanism where if you copy copy and paste something into the terminal, now there’s a warning, which is good. But, again, if the user, like, agrees to it or not, like, we don’t have a lot of transparency. And, of course, what the adversaries do, they just pivot to a different technique. So, again, it’s always a cat and mouse game, and I think the attackers are paying maybe more attention to Apple security mechanisms and then finding ways to to bypass them. So there’s always gonna be a cat and mouse game. Are defenders gaining? Are attackers gaining? I think the good news is it’s kind of in lockstep, and as one kind of pulls ahead, the other then advances. So it’s great job security for all of us. Never a dull moment, But it’s one of the reasons I’m really happy we’re having this discussion because I think when we get to some of the takeaways, some of those will be realizing that, yes, Macs can get malware. Yes. Apple has built a great operating system, but there’s gonna be some things that are left maybe for third party security tools by a design to fill in. And at the end of the day, kind of that additional knowledge and insight into what the adversaries are doing is really how we can start countering, especially more more of the more sophisticated attacks. Attacks. So, Matt, I’m sure you have lots to add to that as well, especially what you’re seeing in your day to day work as well. Yeah. I… I’d I’d add to the Willie Sutton kind of example before too. Like, banks designed good vaults, and they were very well designed, but there still were operational needs of somebody locking them, dual keys, support and control. You had to have the ability to have a security guard, and that guards aspects of what they did in their training, what they do in their execution matters just as much as anything else. And so, you know, I just wanna make sure people take that corollary of, like, at the end of the day, I get frustrated as a as a security human because so many of the things that people talk about as failures are the basics. They they could have been dealt with by the basics being done decently. Right? Like, it it’s so many times. And even when asked, for most people who don’t know, I’m deeply involved in CIS, at least have been in the past, and as a practitioner, use Center for Internet Security’s critical controls. And I believe those 153 safeguards already adequately decide… Define things that we need to deal with in most cases. I I don’t find it often that there are gaps outside of that other than some of the environmental things and stuff that’s covered in IS two and personal and HR stuff. But that said, as a security framework, it’s pretty good. Now trends of the worst day. So I run a charity called msp911.org. It’s part of cyberize.org, which is my legacy charity that I run with a few friends. And I’m a victim of a cyber attack. I I lost to Soda Nokibi as a threat actor, a roughly $3,000,000 in total economic impact as a managed service provider through acquisition we made in Eastern Texas. I called I called Voldemort, and that is because I won’t say their three letter name ever again, which three letter domains are pretty dope. But that said, that sparked me for about eighteen months being sued by almost every client. Every every employee of ours… Of that company we acquired quit. They’d been ransomed three times, and it was operations every time. They never did an incident response on the first incident. They didn’t do a cleanup. I have much longer form of this, but I won’t believe you all with that. But that’s driven my world over the last fifteen years to try to give back and change operations and raise the tide and and do those things. And so now MSP nine one one, when you as an MSP, I hope you never have to reach out to us, ever have your worst day where a threat actor has compromised you and used you as a weapon against your your clients, we take those cases. And we are at case number 59 in the last two years. So I want to kind of share some of my trends and things that I’ve seen from that. If you rewind back to when ScreenConnect had a vulnerability, and I love ConnectWise. This is not shade. This is educational. But when ScreenConnect had a vulnerability that they called slash and grab, it was literally you could put a front slash after ASPX, setup dot ASPX, and you could execute code. But you could also reset up the server, and you could also take over as admin of that server, and that server would have had up to 10,000 endpoint devices on it. The threat actors at that time didn’t make that that correlation. At that time, they were simply just doing a pop the box, gain remote code execution, ransom the box, try to see if we can get people. And so that shift forward to to what we’re seeing today, now the threat actors are much more aware. There are new groups that are targeting MSPs specifically. They’re more aware of the the fact that we have these force multipliers. And if you’re an MSP, think about your operations. If I gain access to one of your employees, can I turn off EDR on systems? Can I put things in groups that would be bypassed from response? Can I do things that not only take away the response that you’re going to have, but also then inject my malware, put in a site that has click fix? And to Patrick’s point earlier, fix has been around for almost two years if I recall correctly on my timeline. It’s been used in Windows environments for a very long time. You’ve seen it pivot to Mac, and and to his point, that’s more of this evidence of this shift to where the money is. So adding to that, these MSPs that have taken these worst days, there’s a certain element that the more mature they get, the more they feel it’s their vendor that was compromised. It’s kind of an interesting trend I’ve seen is the more mature they are, though it can’t be me. It must be my my Mac has been compromised. There’s a zero day on Mac. And in reality, most of the times, it’s not that. It’s that one technician they didn’t lock down. It’s the system they didn’t have set properly. It’s something in that nature, and it’s it’s interesting to see that more maturity means more not me. But also, at the same time, the last three or so cases we’ve taken, the insurance companies that provided for that MSP were saying, we will only look at the impacted devices on your network, and we will only look at the things of yours, and we’ll gather logs from your systems. We will not cross the blood brain barrier to your client. That needs to be their own insurance case, their own filing, their own defer, and if they want to sue us, they can sue us. And what that means if you’re familiar with the term subrogation is at least in The United States, you have the capacitance for that insurance company to sue you as the MSP as a response to what the fault they believed was. Right? And and and I won’t get into the long form of that. But I’m seeing more and more shift of this setting up this tension between you as an MSP and your client. And so it’s abusing trust and and it’s shaking trust. Why did my clients leave? Because they’ve been ransomed three times in this company I acquired. You’re stick around for a fourth? Yeah. That’s a hyperbolus example, but the reality is threat actors are becoming more aware of MACs. Threat actors are becoming more aware of of the 43% of the GDP. It is much more accessible. It is easier to ransom and and gain money from those things. And so you’re seeing several shifts all play out at once, and I’m not trying to be the the doomsayer, but what I’ve seen very well played out is those that are prepared and have good operations have less impact. And the ones that have had this where all their clients got popped, but now only these 12 clients got popped because Johnny that got popped only had 12 clients access, and we did that operationally and managed that operationally so he would only have the principle of least privilege for those systems he needed. If you’re a security practitioner or a managed service provider in today’s world, and you do not have the defensibility of following some framework, following some external source that you are using, and applying that for you and your clients, you’re setting yourself up for failure as this industry shifts, as the threat actors become better and better at reaching the smaller and smaller potential threat… Victims that we’re seeing. So, yeah, some of the things I’ve been seeing. I like that, Matt. That’s very insightful. And I think you also hit on something that I just wanna echo and reiterate that I sometimes we get distracted maybe by the news articles of the sexy, you know, zero click iOS bugs that nation states are using for their targets. And like you pointed out, a lot of times when an attack occurs, people are like, oh, it must be the zero day or something. And, you know, I’ve even seen the vast majority of successful attacks against Mac users. It’s often something super basic, which I think there’s two things. One, it’s somewhat disheartening. It’s like, well, the adversaries don’t even have to have the zero days, and they have your… A very advanced capabilities. But, two, to your point, I think you articulated this really well, is if we actually address the fundamentals and the operations and, you know, did the the basics right, a lot of the attacks would be thwarted. Yes, the adversaries would evolve, but now it’s almost too easy because a lot of the fundamentals are not adhered to or not taken care of. And so I think it’s really important to first focus on those exactly like you said. And then once those are in a good place, a, I think the vast majority of current attacks against Macs would would fail against you if you’ve kind of checked those foundational boxes. And, you know, I think that… That’s just a really good good place to to start. And so I think sometimes we get distracted by the shiny exploits when reality is the the solutions, in many cases, are a lot more foundational. Yeah. Agreed. Nice. And it’s, you know, going back to this idea of the basics and sort of the foundation that we’re on, I I remember… And you had touched on this briefly, Patrick, but this idea of, like, what are the the myths that need to be dispelled? And we know over here, you know, like, don’t get malware. We feel like, at least in this room, that’s been mostly retired, I’m hoping. You know, I think maybe for the average person, maybe there’s still a couple people out there. This is fine. But but even more important I think too is is what’s going on here on the right, is like Apple is doing enough and that there’s, you know, there’s sort of this idea that, well, no, actually, like where does that responsibility lie to kind of, you know, watch out for these these new vulnerabilities? So I’m I’m sort of just leaving that up to you two now as as, you know, what are some of those myths we need to dispel? If you could talk to that a little bit. Yeah. I think it’s really good to reiterate these because especially previously, there definitely was the mindset that Macs don’t get malware. And the reason this is such, like, a catchy thing is this is essentially what Apple had on their main website all the way up to twenty twenty twelve. I mean, the full quote was Macs don’t get Windows malware. But even then, that wasn’t wholly true because there was cross platform malware. But we won’t get into the nuances too bad. But, unfortunately, the general public ran with my Mac is more secure. And to Apple’s credit, that was generally true for a lot of reasons. I think one of the things is as Macs became more popular, there was a lot of good lessons that had already been learned by the larger operating system vendors. So, again, putting myself somewhat back in the day, Windows XP, you plugged in that system. Within ten minutes, it was gonna get owned by something on the Internet. Config or Slammer, whatever the worm at the time was. And so as an industry, we learned some lessons. Like, don’t run with all these open services. Start implementing, anti exploit mechanisms like ASLR, non executable stacks, you know, heap metadata checks, all the things to make exploitation more hard, limit your attack surface. And so as Macs got more popular, Apple was kind of implementing these industry wide best approaches. And so, yes, Macs never have gotten as prolifically targeted successfully as Windows, and I don’t think they ever will be. I mean, if there’s a a a Mac worm that infects millions of Macs, I would be shocked just, again, because of large amount of the security that’s into the operating system. But the problem is because of that, which is a good thing. Right? You could plug your Mac into the into the Internet and got… Not get hacked right away, is Mac users became a little bit of a little bit overconfident, I would say. And adversaries really do take advantage of that now, where a lot of the Mac attacks we see even today, they’re kind of almost socially engineering based where they’re tricking the user into running. We’ve mentioned click fix, which is… Many of you probably know, but the idea is a website or the job interview you’re having, which is actually the North Koreans trying to hack your Mac, give you a bunch of instructions to run-in your terminal window. And you might be thinking, like, I would never run random commands, but, you know, there’s very creative convincing ways for this to be done. And many of these commands, the malicious ones are, you know, hidden at the end, and so the ones at the beginning will actually fix the problem you have. Now if you’re a Mac user who’s not really aware of the threats that are out there and have never experienced an infection on that, like, you’re gonna be super confident and just pretty much run wherever. Whereas on Windows, you might be saying, Maybe I should be a little bit more cautious. I know about malware and and leasing. So we really need to retire, and largely it is. But I think just to put the nail in the coffin that Macs don’t get malware, they most genuinely do. Any operating system does. And, again, especially as adversaries are now more than ever really paying a lot of attention to Macs, very incentivized, especially in the enterprise, Macs definitely get malware. So the next question or the next thing I run into, the next myth is a lot of people say, okay. Cool. I understand MaxScatbauer. I’m gonna try to be careful about, you know, where I download my software from and, you know, not run random commands from the Internet. And I’m like, okay. That’s great. We are moving in a great direction. But they say, I don’t need any security tools because the operating system is gonna protect me from everything. And, again, as we’ve even just shown with ClickJack, which is, you know, ClickFix, which is getting users to basically run the malicious commands, In that case, the operating systems can’t really do anything to some extent, but there’s some other examples where I personally believe that the core capabilities and security mechanisms of the operating system are not enough. And this isn’t a knock at Apple because I think this is a conscious design decision. Apple basically says, we want an operating system that’s a pleasure to use, that is good for the average person. And you have to think Macs were originally designed for, you know, consumers, maybe not as much in the enterprise. Well, in the enterprise, I think there is… The the the the bar should be higher in terms of of the protections, and I think this is where third party security tools come into play. Yep. We talked a little bit earlier about the fact that macOS has some rudimentary capabilities to protect against malware, kind of almost a signature based anti malware mechanism. But the thing is Apple can never afford to have a false positive. Because if they do, you can imagine, like, random person at home, their Mac flags something, and, like, Apple says it’s malware, it’s not like Apple. It’s just a disaster for Apple. Whereas in the enterprise, I think a EDR product can be a little bit more bold with the trade off that, okay, maybe every now and then it has a false positive because there’s hopefully an IT team behind that that can help work through that. So Apple’s built in kind of AV component is very conservative, and we’ve seen adversaries malware, specifically when their malicious code gets flagged, flip a few bytes, and then sidestep Apple’s signatures. So I think this is a great example of, okay. Apple does a lot of great things. They have a really good base, but there’s a ton of room for third parties to supply that layer, both in terms of more comprehensive security, EDR, antivirus, you name it. But then I think there’s a large layer of just managing the devices and making sure there’s more transparency. If the user runs something they shouldn’t, how does that look like in terms of a a dashboard or a scene? And then as Matt kind of touched on earlier, there’s a lot more that also goes on after the fact when a detection occurs. And, again, this is something that Apple just doesn’t lean into, I think, by design. So I wanna hand that over now to Matt and kind of have him dig into it as well. You know, is Apple enough, Matt? What what are you thinking? Yeah. I think it’s a fantastic base that I would start from every day and choose to as my daily driver. I would rather have memory separation. I would rather have not sloppy code in the way I make an OS that’s a 100 years old. I would rather see these bold changes they’ve made. That said, there is still an economics scale challenge, and when we think about even the shift to AI, there’s a speculation that the most valuable things will be data. Data will be more valuable than the thing I could create easily in in distillation of that. So the point I’m making is that when you think about what it takes to defend against a device or a threat a threat actor and threats that are out there, there are threats that happen outside the Mac. There are threats that happen by tricking me to go to a website that’s poisoned, that now has an AITM or an adversary in the middle of harvesting of my token without the right MFA or protections. That’s not anything that Mac can really do something about. I’m still a user. I’m still being stolen from. And so my argument is, I need telemetry. I need data. I need information. I need to know that that user had a DNS query that resulted in me going here, that resulted in a website being pulled down, that resulted in a click fix being copied to my paste bit, to my my clipboard, that resulted in me opening terminal, that resulted in me running these commands. There was… I need that data. I moreover need to know whether that’s malicious or actually just the stuff I should be doing in my day to day job. Right? And so I think the point that you made very, very articulately, Patrick, is that enterprises have more capacitance, but even MSPs bring tools and capabilities and and distillation of this threat intel, right, of what people are doing, what’s malicious, what’s not, and it just doesn’t make sense for Apple to be the arbiter of that. It… There’s too much broad field that’s outside of their space that it doesn’t make sense that they’re that. But in the same breath, even if I was the most skilled surgeon, back to my surgery analogy, and I’m sitting here in the Surgical Room and everything’s lit up and we’re all ready to go, and I’m going to poke my finger through your skin to make the incision I need, I’m not going to do great without tools. I still need a scalpel. It’s going be real rough without that scalpel. And so the argument is Apple brings a fantastic place that you can lay stuff down upon, but you still have to make choices on settings, and you still have to fight the fact that I have this theory, Patrick, called the middle theory that says that products don’t rise much above or fall very much below the maturity of the consuming entity. If nobody’s asking it to be more locked down and more secure and harder to work with and harder to deal with the memory management and harder to have application developed because of those changes and because… If nobody’s begging for that, then Apple has actually been ahead of their skis of doing those things even though they caused problems. There’s many a time that that has caused problems for developers, had them rewrite their trash code to deal with Apple’s changes. So I would laud Apple in that, but in the same breath, I wouldn’t say it’s enough. It’s just the the thing that I need to have the airbags and seat belts in. It may be a great car, but I still need those things integrated in that way, and there’s just so much involved in not only that, but the operations, the management, the decisions. Do I leave that port open? Do I use this thing? Do I turn on the service? Do I not? Those are all operational decisions on how those Mac fleets get managed. So, hopefully, beat this to death. Like, if Ralph Wiggum was here, he’d say, it’s already dead. But, yeah, I think the Smith is dead. Oh, but this is great, and I think the both of you really touched on these… This idea of, you know, where do you get the right data to make these decisions? How do we sort of go about, you know, in your, you know, example of, you know, like finding the right tools? How do you even evaluate those tools? And I know you… This actually was taken from a conversation we had, Matt, about, like, the tool is not the answer, but you can’t not have a tool. And so if you… Yes. Speak a little bit more about that because I think that’s really a great segue into I kinda hit it a bit ago in the sense that, you know, like, you’ve the surgical fleet. But that said, like, how do you even choose which tools? Like, what sets up an operating theater? Right? It’s from guidance from AMA. Right? From It’s the American Medical Association and the guidance of what what makes and constituents a a operating theater. And obviously other things. I’m not a doctor, again, Holiday Inn Express thing. But the the point is is, like, I think that if you are still the smartest guy or gal in the room around security, you’ve failed. You you have to start realizing that we… When we do this in every other world, engineers around bridges say that every engineering guideline is written in blood. Right? Every single bridge rule has happened because somebody fell through the freaking bridge. And so when we get into this, this challenge is, like, we as security practitioners have too long been the smartest person in the room. Well, I’ll just take it to the smart guy. Patrick knows how to deal with a Mac security. I’ll hand it to Patrick. He’s got this thing. It’s some small definable thing. Mac security is just Patrick. Done. When when the reality is we’ve built entire frameworks. Right? There’s an x k c d comic that says, you know, we have 13 competing standards. We’re gonna fix one that makes… We rules them all. We now have 14 competing standards. I love it. Right? And so, you know, what I would say if you’re a practitioner, you should pick a operating framework, whatever it is going to… You’re going to use, whether that be CIS, Center for Internet Security’s Critical Controls, and, you know, and this is NIS two guidance, which is actually, I think, probably one of the best encompassing documents, god bless its problems, that I’ve re… Read recently. But also, you know, NIST two or or Australian’s essential eight or CAF or… There’s so many. Pick one and start working from that. That’ll tell you, okay. Guess what? CIS 10 .1 says I need anti malware capacitance. Right? CIS nine .1 says I should control the browser and be able to manage the browser and its extensions and further in nine and email clients and other things. And as you start evaluating your Mac security through that, you’ll start seeing where there’s not something natively there to make that possible or there’s not something there to make it scalable. And that’s the other part. You have to make a profit. You have to make a profit in a screwed up economic world where the reality is you’re not gonna get all the dollars you want. You’re not gonna be able to do everything you wanna do, and so you have to find that greatest good impact and how do I do it at high scale and high speed. And so I think that, you know, while that does sound like a very veiled pitch for Addigy, it is a very veiled reason for why I used Addigy to scale my world as a practitioner because I could bring those things at least in some degree of normalcy to a known good space and a known decided upon space from a risk posture perspective. And, Patrick, you… I’ll toss this back to you. You said it so well earlier of, like, you know, enterprise might have higher risk, and they’re willing to take more posture and have teams to deal with it, and so they can maybe have more false positives, whereas to the consumer, they can’t. And then it comes down to, like, you have to figure out where your risk posture is, where your actual risk is, and make decisions based on that. And anyways… But, yeah, I think the the point is operations and security and hard choices are often the security, but you still need the tools. You can’t do it without it. You can’t scale it without it. Yeah. I love this discussion because, you know, the Objective C Foundation created a lot of free open source tools. And at the beginning, I was like, this is the solution. And then it’s like, no. As Matt said, this is a really good, important first step, a foundational component. But that magically doesn’t solve anything. And so I think there’s another thing I wanna touch on, you know, on the slide I mentioned. It’s like, who’s behind the tool? And so just like hackers, malware authors kind of pivoted to macOS because that’s where the market share is, we saw a lot of vendors doing that. And I, you know, can just imagine discussion where there’s a, you know, hypothetical company. They have a really mature Windows security product that’s really well recognized in the industry. And, you know, they’re saying, oh, wait a minute. Now, you know, 84% of businesses run Mac, the market share of Mac’s increasing. Like, there are more targets. I don’t know if they use that same term. Customers, I think, would be the appropriate term. Yeah. Where… But it’s the same, like, mindset of the attackers where, okay, there’s these Macs that potentially could run our software. In the context of security software, it’s good. In context of malware, it’s obviously obviously bad. But macOS is really, really different than Windows, and especially from the context of a security tool. I grew up on Windows, my initial reverse engineering malware analysis, defensive and offensive. Splunking, let’s just say, was all on Windows. And so when I started on Mac OS, yes, of course, there’s parallels. There’s, you know, memory, CPU, stacks, and all that stuff. But there’s a lot of very specific Mac isms, Apple isms that if you’re writing a security tool, you really need to live and breathe. And so what we see is a lot of vendors, a lot of companies who maybe existed or were very well known in the Windows space are kinda jumping on the Mac bandwagon because it’s maybe trendy or, you know, the sales and marketing team says, hey. Like, there’s there’s new potential customers. And then they release a Mac security product. And the crazy thing is their Windows product can be incredible, but their Mac product is just like a dumpster fire. They do not have parity there where their Windows product can detect perhaps new zero day exploits, ransomware. Their Mac one is, like, doing basic signature scanning. And it’s largely because Mac is so different that you really, in my opinion, need a dedicated engineering team that, like, lives and breathes macOS. And since macOS in some senses hasn’t been around that long, most of us have kind of cut our teeth on Windows. It’s a learning experience for us also in in the space. So for example, there’s not a ton of security engineers focusing on on macOS. So I’m a big fan. People always ask me all the time. Patrick, how do I pick a vendor? And I say, okay. Look at ones that are, a, either just focus on Mac. It’s like kinda do one thing, do it well, or just Apple, let’s just say. Or ones that really dedicate, I would say, you know, a ton of their engineering and focus on on macOS. Because the companies that are doing cross platform stuff, Windows is still 70% market share on on… In in in the enterprise. So it makes sense that that’s where all their resources or most of their resources… The majority of their resources and dollars go, especially that’s where traditionally it’s gone. So who’s behind the tool, I think, is a really important question. And not just looking at track records, because someone can have a great Windows track record, and on on Mac OS, it’s it’s it’s totally new. So I always say, you know, look for companies that are putting in the time and effort, putting in the resource… Research, putting in the the r and d money, putting in the focus on Apple because invariably, it goes to follow that their products, unless something goes very wrong, is gonna be, in my opinion, far superior than, you know, other ones who half or more of their time are distracted by Windows. I feel like Matt has something to jump in and and hopefully agree. But if he disagrees, let me know. I agree. You’re triggering me on something that was earlier in my career. This was about seven years ago. I won’t name the vendor and I won’t name the researcher, but I was having a pen test done, a static pen test done on on a very large client that was mostly Mac. And so representative device that was used was a Mac, and so they were testing a HTTP… A reverse shell over HTTPS modality. That was one of the tests that had to be done, and it was failing to be caught by the EDR. We get involved with the EDR team. I start talking to the EDR team, and the EDR team admits in front of accidentally this researcher that I brought in the room that was the pen tester that they had not been inspecting Python for three months. Oh, man. And and it’s… Your point, it’s a massive vendor, and the point was, like, they had… They got caught by the change that Mac made, and I don’t remember exactly what it was, but they just didn’t have the inspection capacitance, they weren’t ready to make that change. And so, yeah, you triggered me on this one because that one became a huge security hubbub. You could probably find it if you wanted to be an OSINT person because the researcher then wrote an article about that and doxed that company, but that’s okay. But that is a good point because my understanding is, like, Python is not natively installed on Windows. I haven’t dabbled there for a long time. And so, you know, just the the the environment is so different on on macOS. And to your point, I think you touched on earlier, one of things I like about Apple is they are very okay, let’s just say, with, you know, making changes. They throw out leggity… Legacy stuff, deprecate stuff. And for dev… Developers, that can kind of be a pain. When I started writing, you know, for example, a firewall for Mac OS, it was suggested that you do that in the kernel. And then Apple kinda said, hey. Wait a minute. This is actually not a good a good reason. In retrospect, that was brilliant of them. They said, no more kernel code. Here’s the user mode framework you can use. Awesome. But that did mean you basically had to fully rewrite your 100%. Firewall, which Yeah. Is a lot of work. Windows is never gonna do that, and that’s why we And economics don’t support it, Patrick. Nobody’s gonna pay you more for that firewall because you have to spend five sprints fixing something. That’s that’s just expected as the cost of doing business. And I I I love that you’re bringing that up because it is… In my opinion, I I respect them a lot for that, and we’re gonna get into trust too. But I had a friend of mine that worked at Apple for a very long time, and he told me that he still, to this day, has to do… I think he’s still there, as I remember from… It’s a friend of a friend, but it doesn’t matter. But he still has to do reviews of whether he should have access to something. That’s operational purely, saying you as an internal person has to do reviews of whether you should still have this standing access. That’s… That is only operations. Right? And so That’s amazing. The other thing you get into trust is how do I trust the company that I’m working with, right, to that point. Yeah. And so one of the the risks though is as Apple changes things, which I think we all agree is in the long run the best thing, but if the company behind the tool is not intimately familiar with macOS… And I remember doing this myself. They changed their, like, code signing certificate, and, you know, one of my tools was, like, looking for changes in code signing. And, you know, that was something I had to very quickly say, oh, okay. Well, this is still signed by Apple. Trusted. But, yeah, they’re they’re they’re leaf… The name of their leaf certificate changed. And that’s, like, you know, a big change that could potentially indicate something’s wrong on a host. Maybe malware’s tamper… Tampering tampering with it. But, no, it’s Apple just updating something. But if I was distracted by, let’s say, Windows tools, I might have missed that or missed, for example, the… Your your Python example because Apple does change things very quick. And so if the team behind the tool is not laser focused on Apple, in my opinion, there’s gonna be gaps that come through just exact… Exactly like your your point with Python and adversaries are sorta, like laughing all the way to the bank. It’s like, great. Bring your Windows tool here. We’ll like Exactly. We’ll run Python and just, you know, walk out to the to the Internet. So, yeah, I I really like that the tool is not the answer, but neither is not having the tool, and it’s really important, the trust and and and also the team, the company behind the tool, and how much blood, sweat, and tears they’re pouring into the, you know, Apple version of their tool, which is hopefully the only version that they’re they’re building. Yeah. Really well said by both of you. And I I I wanna dive in a little bit more to that that shared failure piece. Patrick, can you speak a little bit more to that? Yeah. I think it’s just kind of like Matt’s point where people will deploy the EDR product and maybe don’t dig into it as much to figure out what it’s doing and then figure out three months later that it’s not monitoring network traffic or it’s allowing any Apple binary to run, which includes and Python, which a lot of malware abuses. So in some cases, it’s maybe not configuring it incorrectly. It’s just having a really intimate understanding about what the tool does and doesn’t. And I would say if you don’t have that understanding, in some cases, that is a shared failure. I would say it’s a shared failure on the vendor, maybe not to be more transparent of the limitations. But I think also we have some responsibility for the tools we install and deploy to do our own vetting of them and not just taking what the vendor says as as absolute truth. Wow. Very nice. So thank you both here. And because we’re talking about Frontier here and you have a lot of that historical knowledge to kind of read the tea leaves, so to speak, what does AI actually change here? Like for the defender, for the attacker, you know, what are some things that maybe we the both of you sort of could see, hey. You know, like, this is, you know, how I could see things coming out in the next five, ten years, or even, you know, hey. These are some things I’m still a little bit skeptical of. Like like, let’s talk a little bit about that. So let’s let’s do this. I’m doing a stage presentation in… Oh, goodness. Where is that? Copenhagen. Yeah. That’s right. Copenhagen here in a few months. And one of the… It’s called cybersecurity twenty thirty, and it’s asking us to pause it. What does it look like in 2030? Like, what does five more, three more, two more years look like for us, in this case, three? But I think code has been built with one specific cadence. Imagine you in the audience are a product owner, and you have the ability to either fix some bug that’s existed a long time or do the new feature you’ve already promised to sales for the last three sprints, and sales is like, bro, got people ready to sign up. We need to hit our third quarter numbers. Which one gets the sprint? It is… Unless you’re really well structured as a company, you’re not typically dealing with this one. You’re dealing with the one that makes you money. So that has built, in my opinion, ****** software. We all use ****** software. It is part of our day. It’s part of our life. It has built ****** software, with some examples that might be excluded from But the point is is that there hasn’t been a capacitance or a reason necessarily to fix it. Threat actors can’t enumerate everything. Right? We’re finding vulnerabilities in Linux that were 20 years old, right, with some of these things. But, like, the reality is we now have this increased capacitance of threat actors and researchers alike to do tests, to enumerate surfaces they wouldn’t enumerate, to try things they wouldn’t try, to put connections together that wouldn’t happen in a way that’s fairly scalable. I think that as that becomes more viable, we will probably have better code over the next five years. I I I think it’ll just get better. Now granted, anybody in the audience can slap me. There’s gonna be a lot of vibe coding that might make that not right. There’s a lot of things that are gonna change. But for those with the applications, software development life cycle that give a ****, code’s gonna get better. I I think that’s a reality of of what’s going forward. I think at the same time, while we discussed that Vulpocalypse hasn’t really arrived, like, haven’t gotten to a point where this quote, they’re gonna find every vulnerability and everybody’s gonna be dead and it’s just gonna end right now. That’s kind of this belief that news has tried to put upon us from from all of that. And it’s even been pushed by some of the things. I’m doing a talk called giving swords to our future AI overlords of this discussion that, like, we shocked an elephant at one point. Like, we we put an elephant and electrocuted it for media histrionics. Like, we did that. But we also now have models of AI escaping their controls and attacking somebody and creating criminals. Like, straight straight up, we we did… All of the major frontier models decide that their stuff just accidentally escaped my my sandbox. And the only one thing that I had as a job to assign me, that is media histrionics. That is the expansion of saying, look what mine can do. Look what mine can do. We’re in a weird world right now in my opinion, and and we’re seeing this shift happen. But to get real, when we looked at, one of the predictions I’ve made is that as we see one vulnerability be found, we’ll see threat actors pick and pick and pick and pick because they found it. And and Patrick, you’re smarter at these things, so I may… Linda, you answering this. But I I believe we’ve seen, like, in Abel, they found one vulnerability in in central, and then after that, they found another one, and another one, and the threat actors kept picking at that wound. Right? That that wouldn’t have been done but by the most sophisticated of actors, but now it can be done by a harness. I can have my Claude bot just do that. And then at the same time, when you talked about Patrick, people on Macs have been smarter about where they download their software and they do those things and maybe protect… Well, no. Now we’re doing Claudebot or OpenClaw and slapping it on our machine and grabbing 500 MCPs that install 4,300 packages in Python that you don’t know what any of them are. Right? And so I think we’re moving towards a direction where the more bespoke the the software, the more bespoke the attack against it at the same time. And you said this before, threat actors gain, we gain. Threat actors gain, we gain. But now at a world where we’re making software yourself and you’re using that brand new Mac to run some local LM and run-in with these packages you’ve pulled down out of code, like, there’s so many challenges. And I I know I’m going off on a on a rant here, but I I think in the long term, though, companies like Apple, and I’m not an Apple fanboy. I’ll tell you, I didn’t buy an… My first Mac until two years ago or three years ago, and was for that same very purpose of running an LLM locally on my machine with shared Windows, memory resources. So, like, I’m gonna straight up tell them myself. But that said, I I have become a convert for these things, and so I think we’re gonna see more that Apple has always been in a position to break eggs, to fix things, to be that trusted partner, to do the stuff internally that’s painful. Right? And and I do believe we’re gonna move towards a better and more secure operating system that’s already been a good base to start from. And, Patrick, you can probably take it from here. Yeah. I like that. I think you hit on many of the really important points. And there was one security research that I made a really good point online that I liked, and this is when fuzzers came out. I think it was, like, you know, early mid two thousands and You’re dating yourself a smidge, Patrick, with with early days of fuzzing. But, yeah, go. For anybody that doesn’t know, fuzzing is trying to find a directory that you don’t know the name of, and you can do it by inserting a bunch of tests until you get to that one that says, alright. Fair. Fair. Fair. Fair. And and when fuzzers came out, like, bugs were, like, raining from this guy. And everyone was like, oh, wow. And, you know, so AI think there’s some parallels here where I think any new technology can be used for good and for bad, and, you know, we could discuss this forever. But we do see software vendors pushing out patches that now have the most patch bugs ever, Apple, Chrome, everything. And at the last Chrome update that came out, 90 plus percent, I think, of the bugs that were patched were found internally by Google, really showing that they were ramping up their AI use. And so that to me is is a win. Matt, you said this really well. I think AI is definitely gonna make code far better. I run it on my tools, which I have really, you know, lovingly written, and I find some embarrassingly bad bugs. No big security issues. Yeah. But still, like, things where I’m wow. Like, how did I miss that? And so it really benefits the defenders. They can find bugs in their code. They can really just empower, I think, security teams. Exactly. I loved your your argument. Previously, like, the new features were the shiny things. Well, now you can, you know, have your AI agent help patch some of the bugs. Right? Unit tests. That’s what I use. And so I believe, like, the code I’m releasing that other vendors are releasing, the quality of that is going to increase. Agreed. Vibe coding aside. Obviously, though Thank you. The attackers are also using AI. I’m sure they’re using it to to find bugs as well. I think one of the big advancements is the ability of AI to… Once a bug is patched, you know, developing a… What is it? N minus one day exploit. Yes. The timeline and the the the time window and the skill required to do that is, like, drastically Yeah. I can use a Ghidra MCP and reverse engineer something really quickly. Right? Like, those those kind of things. Point, To the skill sets and and capabilities are there for that diffing. But what have we always told people? Patch right away. Because there were already sophisticated adversaries and very skilled teams that were doing that maybe not at scale. So if the takeaway is, okay. And now this is one widespread, and so patching becomes essential, like, day zero, That I think is another win for security because that really goes back full circle to the beginning where we talked about what are the basics. It’s like when Apple releases a patch, get that installed ASAP. We always said that was good advice. I think now AI is showing that, yeah, you really need to hop on that because script kitties are now able to weaponize these these vulnerabilities. And so at the end of the day, there’s maybe just one example of, okay. This actually drives, security. So I think it’s something where there’s pros and cons. I’m currently on the fence. No. Not even. I’m currently on the side of that it benefits defenders. They’re the ones with all the tokens, and I think they’re the ones that are leveraging AI. You know? We see Apple, Google, these big vendors patching a ton of bugs. Sure. The adversaries are gonna benefit it as well, but overall, I think in the long run, you know, code is gonna is gonna be more secure than it ever has been. And a lot of exploits gained access to systems or or… Because of vulnerable code. And so if number of bugs are reducing, again, that’s a win for the end user. Even if getting there is rocky. Yeah. Wow. So I mean… Yeah. Wow. Thank you both. I think this is this is all gonna be good for us to kinda see, you know, what what unfolds. Right? And who knows? You know, it’s not gonna take us years. It’ll be months or weeks. And I I really appreciate the the both of your perspectives there. And so I I think just kinda wrapping things up here, knowing we’re almost out of time, if we could kind of summarize, you know, because I I feel like I could spend another two hours, and the both of you kind of like digging into a lot of the stuff that you said, and who knows, maybe we we have another session there. But if we could kind of leave folks with a sense of, you know, how who do you trust? Who… How can you check? You know, how to make sure someone’s a trusted adviser just moving forward given everything we just talked about. I mean, what what do we wanna leave people with in terms of, you know, what can you kind of walk away with here sort of feeling like, okay. This is what what I need to do next, or this is kind of how I wanna, you know, go forward with my security compliance, things like that. Well, you know, you bring to this point of the supply chain risk and the supply chain challenge and trust, and and and it goes back to a talk when I was really young of interdependency. As a kid, you’re like, I wanna be dependent. I wanna be independent. Well, you’re never gonna be independent. You’re interdependent. You’re interdependent on that guy not hitting you in the street. You’re interdependent on the street being viable and the signals being right. You’re interdependent. And so I I think what needs to happen for you to figure out who to trust and where to place your trust is to have a trust framework. I am stealing this from Rob Reck. He is our chief trust officer at PACS eight, and he says three things. He says, number one, you have to have a you have to have a one to one say do ratio. If I say I’m going to do something, I’m going to do it. If I tell Patrick or Angela that I’m coming over to hang out and do what we’re going to do, and I don’t show up, at some point, you won’t trust when I say I’m going to show up. There’s there’s a one to one there. But that’s not always possible. You’re gonna fail. There will be failures. You’ll make a mistake. You’ll miss something. You’ll push a patch that you thought was gonna solve the day, it missed something. You’re you’re gonna make mistakes. So the second part of trust is having ability to have hard conversations first. If you mess up as a kid and you come in and go, hey, dad. I’m so sorry. I messed up the lawnmower. I was doing something stupid with it. Like, is that better than dad going to hop on the lawnmower in three days and he can’t mow the grass and it’s hot and he’s mad, and now he’s having to figure out why his lawnmower’s broke? Which one’s better for you in a relationship with trust? I don’t want you to use my lawnmower no more. Don’t trust you. Right? But then the third one is one that can’t be faked because you can kind of fake your way through those two. You can be very disciplined and do the things you say you’re gonna do. You can be very disciplined and and speak first when it’s hard and have some introspection and tools and systems for introspection. But the last one you can’t fake, I don’t think, which is having aligned incentives. If my if my job and my underlying, like, card in in life is I have to kill Patrick Wardle, then no matter how much I come over and hang out and have beers with him, there’s no reason he should trust me. I’m going to kill Patrick Wardle. That’s my mission. We do… We have misaligned incentives that Patrick wants to live. And so there’s that point of, like… Yeah. So there’s a line incentive. So I think when you take that into a framework, makes sense. Choose a vendor that that that has a pretty good track record of releasing when they say they’re going to. They take bug bounties well. They have good re… Responses to their to their internal researchers and external researchers. And then when they mess up, they say something. They’re honest. They’re transparent. They’re front front about it. Right? And then the last one is that you you were able to determine that your incentives are aligned. And and that’s the hardest one to do, I think. But, Patrick, maybe you can speak towards aligned incentives a little better. Yeah, Matt. I like exactly what you said. I mean, to me, you know, I’m gonna start with kind of the broad apple. One of the things that’s been… We’ve touched on this a few things. I… You know, at the end of the day, yes, they are a company beholden to their shareholders, and their goal is profit. But I feel like they do that in a way that’s largely responsible, and I’m really passionate about their approach to privacy because I think security often follows through that. And so when I buy something from Apple or when I use an Apple device, you know, I’m confident that it’s it’s not spying on me, that Apple doesn’t have the incentives to track my browsing habits and all these things to sell me more stuff because, you know, they built this great ecosystem. They build incredible hardware. They’ve really taken this other angle, which is pretty rare in terms of other, you know, large operating system vendors. I I really like that. And then another extreme, you know, like, working with Addigy has been amazing. They’re super supportive of, like, the foundational stuff we do for the community in the Objective C Foundation. And so, like, that to me just speaks to the aligned incentives where vendors that I find also realize that investing in the community is an amazing thing to do. You know? Addigy, like, helps fund our student scholarship programs, which brings, like, kids to our conferences, our trainings. They then meet with companies that are hiring, puts them on an amazing trajectory. That’s just a win win. And that, like, doesn’t generate profit for Addigy. And so, yes, I’m using that… Them as an example. But I think that’s a great thing of looking for vendors or companies that kind of are doing the right thing. And, like, that sounds super, like, cliche, but I am still really passionate about that. And I still think there’s companies out there that you can take a step back and say, are they only obsessed with profits? And I think Yeah. Apple is another example of, sure, they love profits, but I think they’re generally trying to make the world a better place. And so to me, those are the companies I’m choosing because I think those are the companies that when a hard decision comes, like being transparent about a screw up or something else, those are the ones that are gonna be, let’s just say, emotionally mature enough to to to own up or have that hard conversation. And I don’t think all companies are like that or even close to that. And so looking for the ones that I think, you know, feel like have a heart or try to do the right thing. To me, you know, maybe I’m a little hippie, but that to me is is is one of the things I look for when figuring out who to trust, who to work with, who to collaborate with, and who to align with. Wow. Thank you so much for that. And it’s… As a philosophy lover, I love… I mean, just like what the both of you really are doing for education. I mean, like for me, like that word really means like to bring out the best within someone. And I… I’ll just give a nod to that there and you know, just have really enjoyed this discussion. I know we sort of went into, you know, like kind of what we wanna ask our vendors. We’ll sort of, you know, leave people with a little bit of this. And yeah, I really just kinda wanna, I mean, give the both of you sort of a round of applause here. Just, I mean, all the work you’re doing for the community, and all the work that you did even just here to sort of give people a sense of what is this new kind of world we’re dealing with here. And I’ll I’ll close us out with a little bit of, yeah, where where can folks find you both, and sort of follow some of the work that you’re doing, and, you know, just kind of follow along on your journey just as you continue to, you know, educate the rest of the community about what’s going on. Yeah. So I spend a lot of my time working with… For the Objective C Foundation. So if you pop over to objective-c.org, you can learn about all the cool things we do. Angela, love you talked about education because as I get older and hopefully wiser, I’m realizing that’s, like, such a essential thing to focus on. Perhaps naively, think many of the world’s problems are because of lack of education and critical thinking. You know, it’s probably more nuanced about that. But, you know, like, through the foundation, I’ve seen that when we connect with students and empower them, it really sets them on incredible paths and really, exactly like you said, Angela, empowers them and and and brings that out. So check out objectivec.org. There’s free tools, free books. We do free student conferences. I would say in a nutshell, we are really focused on education and helping things. And so there’s a lot of cool resources for people to learn more about Mac security. And, you know, hearing Matt talk about some of his nonprofits too, it’s, like, equally in inspiring just the goal of him helping other people. So, Matt, where can people learn more about what you do and connect with some of the community focused stuff that you… You’re doing? Because I’m gonna go check those out as well. And it’s cool you talked about education. I I was a pretty good engineer. I wouldn’t say I was a great engineer, but I was a pretty good engineer when I was working in in in tech. And I did a life plan where someone said, Matt, you you keep stealing ability for other people to learn by doing, and you’d be better off as a highest and best use by educating, right, and by teaching them how to critically think. So you you triggered a point for me on that, Patrick. But that said, like, I’m involved at PACS eight, obviously. Addigy, you can find them there. But my noncommercial interests, I I run a charity called Cyber Rise Inc, cyberrise.org, as well as msp911.org, as well as frameworkmaps.org. And in fact, I’m really looking for community involvement. We take and break down cybersecurity frameworks into their taxonomical elements, we can actually map products and say, does Addigy help me with? Oh, four dot one by the extensibility of management and configuration. Oh, these other things that I can all do to that. So yeah, so find me at cyberize.org or any of the three charity programs we run there. And then generally just LinkedIn. Please connect with me on LinkedIn or say you were in the Addigy or I won’t. I got bit by a deep fake one time, and so I just don’t approve connections anymore unless there’s some corollary as to why. But, yeah, please reach out on LinkedIn and and help me out with the mission. Thank you. And, Patrick, it’s it’s interesting when you find other people cut from the same cloth that just really wanna make the world a better place. And and I think as AI becomes more and more prevalent, humans will want humans, humans will want to share with humans. And so I I I love what you’re doing, man. Yeah. Thanks, man. Likewise. It’s an… It’s inspiring. Wow. Well, thank you both so much, and we’ll we’ll cut now to a break here, but thank you all. I hope you’re leaving this session a little bit more confident and inspired. See you soon.
84% of Businesses Run Macs. So Do 100% of Attackers:
An Apple Security Panel
Patrick Wardle, SEO at DoubleYou has spent over a decade inside the actual malware. Matt Lee, Security & Compliance at Pax8 sees MSPs on their worst day. In 40 minutes they’ll work through what’s really being exploited on Macs right now, where Apple’s built-in stack ends and your responsibility begins, why deploying a tool isn’t the same as being protected, and what AI has genuinely changed — for attackers and defenders both.
Speakers: Matt Lee, Security and Compliance Senior Director, Pax8
Patrick Wardle, CEO, DoubleYou
Angela Diaco, Sr. Product Marketing Manager, Addigy
Welcome back, everyone. We’ve got a lot to show you today. So let’s go ahead and get right into it. The future of AI in Apple device management starts here. A quick word on kind of who you’re spending time with in this session. I’m Catherine Davis. I lead product management here at Addigy. I’ve been in the Apple management space for just about fifteen years. I’ve done everything from help desk support, being a systems administrator, over to being in product management for a couple different Apple MDM tools. So I’ve seen a few things and have some more stories if you ever wanna share. Now, we’ve also got Joel. He’s our principal product manager who’s been building and shaping everything that you’re about to see. He’s been with Addigy for nine and a half years, and he oversees a lot of our security, compliance, AI, reporting, and other core areas of the product. I’ll go through and share kind of our philosophy and the high level overview, and then Joel will take you hands on through some awesome live demos. Before we go ahead and show you anything new though, I wanna talk about why we built it the way we did. So generative AI has had a rough year in the enterprise, arguably, couple years. MIT’s State of AI in Business report, covered widely, including by Fortune, found that 95% of generative AI pilots at companies are failing to deliver a return. It’s not just a fringe number. And it’s not just a quiet failure to launch. It’s active backlash. When Slack updated its AI use of customer data, the pushback was loud enough to make headlines. When Zoom changed its terms of service around AI training data, people noticed within hours, and it became a trust story, not a feature story. A lot of products have added generic AI chatbot experiences. You’ve almost certainly used something like them. Maybe they summarize a dashboard, answer a question, draft an email, etcetera. It’s fine for what it is, but in my opinion, the real test that actually matters, and the thing that we here at Addigy have built our AI offerings around is one critical question. Can we trust it? That question is really our whole starting point. We’re never doing AI for AI’s sake here at Addigy. Everything that we’re about to show you does real work to solve real problems. It doesn’t just talk about it. This session’s going to move forward in three parts. So first, you’ll hear me talk a little bit more about our philosophy and how we’re building tools to help our customers in a structured way so that it builds as much trust in the data and the underlying intelligence and tool set as possible. Secondly, we’ll show you some of what’s new and what’s coming next. Joel will showcase some very cool things in this part. And third, we’ll talk about how you and your team can get started and upgrade what you do today with device management by bringing another level of intelligence in for your Macs. The high level of it all is that Apple device management can quickly get complex. And there’s a lot of moving pieces between the controls we get through MDM and DDM, as well as what is possible via a local agent. A lot of thought and care goes into how things work together on Addigy’s side in order to make things as simple and effective as possible on your end. Our approach to AI is really no different. AI is a tool that when used correctly, can be very, very powerful. And when it’s used incorrectly, can cause a lot of work. Based on that, we’re approaching this in a way that gains momentum in terms of what we can see and do, while still being cognizant of any guardrails that need to be in place, and ensuring that our data governance is where it needs to be. All of this is keeping trust as the core test for the efficiency and efficacy. This should look familiar from Jason Depp Barn’s keynote earlier, but I’d like to revisit it quickly from a product leadership perspective. This is a view of our capability map with things building on each other as we go. Some of these things are available for testing now. Some are sneak peeks into where we’re going. Stay tuned to listen for what’s an active beta versus coming soon, as well as see some demos from Joel. Going over each very quickly, we have the MCP access, which is the full MDM control plane exposed over MCP. We also have some guardrails in place, so that you’re not accidentally damaging your environment. AI monitoring. This gives visibility into AI usage across the fleet, shows you which tools, which models, and on which devices. AI compliance. This is the AI standards and governance enforced as a policy. This runs right along your side, your other compliance benchmarks. AI script helper. This assists in natural language to generate production safe scripts right within the Addigy console. The AI report builder, this asks for the report that you need in, again, plain language, right in that Addigy console. And then we’ve got Fable DNS. And this is our internal code name for what we’re working on to tackle the problem of dynamic AI DNS, shadow AI discovery, and agentic egress governance at that network layer. Everything is focused on the methodology of observing and orchestrating. So that your team can tune each each capability to what works best for you and your organization. Whether that’s just observing your environment or you’re moving forward towards autonomy and full automation, the choice is really up to you and what you’re most comfortable with. Our job here at Addigy isn’t to force decisions or force automations, but to offer the best data and tools to make our customers’ jobs as easy as possible. So with that, today, I’m happy to announce our lineup of new capabilities that help bring the power of generative AI to your organization in a productive and secure way. Our mission is simple. Build AI for Apple IT with the trust layer that you expect. We see three places where AI really earns its keep. It reduces friction when managing Apple devices, even if you live in a Windows centric world. It improves productivity by cutting the time it takes to execute and scale your organization’s playbooks. And finally, it aggregates information in a way that’s clear and actionable for you, your clients, your users, your team. All of these new AI capabilities are going live with our intelligence suite on October 31. Going a little bit deeper, I think about these features and what’s coming in four buckets. And each one is a stepping stone to really earning your trust. Do it easier. AI workflows that are meant to enhance existing product features by taking on the annoying or hard manual parts without taking away your control. Prove It. Features that show your work to clients, to leadership, to your own team, whoever you need to showcase that value and what you’ve been doing. Delegate. Once you’re ready, these features let you hand off entire pieces of work that you’d otherwise have to do yourself entirely manually. And last and most importantly, govern. The controls that put you in charge of AI in your organization. Wherever you are on your AI journey, all in or arms crossed, there’s a bucket here for you. We’ll start where most people start, making your everyday work easier. So now I’ll hand it over to Joel to get into the most exciting stuff, the demos. Thank you, Catherine. As admins, we’re constantly needing to locate and track devices by some criteria, whether it’s serial number, the user on the device, OS version, uptime, or a combination of these. Today, that means building complex filters and queries, knowing Addigy device facts, and combining and or or conditions and tweaking until things show just right. It gets tedious and frustrating pretty fast, especially if you don’t have deep Apple or Addigy knowledge. And that’s where smart filters comes in. You no longer have to spin your wheels figuring out which device facts to pick or which filters to stack. Just describe the devices you’re looking for, and smart filters finds and displays them for you. Let’s see it in action. As you saw, you can simply type find devices that have been online for ninety days with high CPU, locate all devices with a SentinelOne threat and Gatekeeper disabled, or find all devices below Mac OS 26, and smart filters takes it from there. Simple AI features like this remove the everyday friction and let admins get straight to the outcome without needing to know every corner of Addigy first. As IT admins, we’re constantly building, editing, and deploying scripts across our fleet. Scripting is how we create powerful customized solutions for almost any scenario, whether it’s software deployment, device monitoring, user notifications, and more. With a few good scripts in hand, anything feels possible. The only issue, scripting is not easy. Getting the best results takes real coding expertise plus knowledge of specific Apple and Addigy binaries. And that’s why we’re happy to announce AI Script Assist. You can now prompt a script to life with the same effort it takes to Google for one. With AI, context is king. Frontier models are great at writing code, but they lack the domain specific details that make all the difference in an app or environment. Script Assist goes beyond generic AI script generation by leveraging deep knowledge of the Addigy platform. As for a script that prompts a user to restart after thirty days of uptime and it doesn’t invent new prompts, It uses Addigy self-service notifications. Ask it to pull device information, and it reaches for device facts and Addigy’s auditor binaries and recommends saving the result as a custom fact if one doesn’t already exist. And Script Assist isn’t just for new scripts. Point it at any ex existing script in your environment, your scripts catalog, a software installation script, a custom fact, and ask it to analyze it. You’ll get feedback and recommended changes almost immediately. One thing that will never happen, changes to your scripts without your approval. You’re shown a diff between your existing work and the suggestion, and nothing changes until you press approve. The AI does the typing, but you keep the judgment. Let’s see how this works. That’s AI Script Assist. It prevents coding from getting in the way of you achieving the outcomes your organization is counting on you to deliver. We hope the AI Script Assist not only saves your team time, but also opens up a new world of possibilities for what’s achievable in your environments. If an IT admin patch is a 100 pieces of software and no one knows about it, did any work actually happen? We understand how important it is to prove the work that you’re doing, and so our next feature does just that. Building the report you actually need has never been simple. Prebuilt reports get you 80% of the way there, but that last 20% is where the pain lives. The moment you start customizing, you’re overwhelmed with options. It could feel like staring at the cockpit of an airplane without any training. Generative reporting removes that UI friction entirely. It gives you a friendly chat interface for generating quarterly business reviews, compliance reporting, life cycle and OS tracking for your devices, and more. Type the information you wanna see about your fleet, and it builds the full report. And you could keep chatting until it’s just right. Need one or two more charts or colors that match your client’s design language? Just ask, and it makes the changes in real time. Let’s take a look at this in action. As you saw, it only takes a brief sentence and a few minutes to build out just the report you need. From here, you can save the report and share it with your team, and it’ll automatically stay up to date. We think this feature will make proving the value you add to your organization a breeze. This is where the busy work ends and the fun begins. For those who have honed in their AI skills and feel confident in delegating work to AI, we wanna give you the capability to do so safely. Many admins already have their own AI agents, and so we wanna give your agents access to the Addigy platform as well. That’s why we’re happy to introduce the Addigy MCP server, which enables you to connect your existing AI agent directly to Addigy. The Addigy MCP introduces over 200 tools hosted by us so you could connect in minutes, unlocking a true headless experience for Apple device management. Here’s some things you should know. First, every single call runs as you. It taps right into your user or API permissions. The AI cannot see a device you cannot see or touch a policy that you cannot touch. Second, anything that changes state stops and asks. You get an approval prompt before a change happens. The AI will propose, and you will always approve. And third, some things aren’t in there at all. Wiping a device, we left it out on purpose because that’s the type of capability that erodes trust if misused. The Addigy MCP allows you to delegate entire workloads to your AI agent. It can build policies, assign devices, create custom compliance benchmarks and device facts, debug devices with real commands, and build reports that span across all your vendors. Here’s a quick demo of the Addigy MCP in Claude. The Addigy MCP may be the most powerful AI feature we talk about today. In the demo, you can see how we can configure a whole policy tree, generate reports about our Addigy organization, and even push Pivo apps directly to devices all within five minutes without ever logging in. Over time, you could build and save AI workflows through skills and prompts that enable you to delegate repetitive tasks and automate away the tedious parts of your work, creating more time in your workday and accelerating growth. Everything you’ve seen so far has been AI working for you. The last bucket flips the conversation. Your users didn’t wait for permission to bring AI to work, and this is about governing the AI that’s already on your fleet. Users are installing and bringing an array of AI tools to work without permission, creating all sorts of issues for your security team. Our new AI governance benchmark is a set of 30 different AI controls built on the same compliance benchmark framework you already use to support CIS, NIST, Cyber Essentials, and more. If you know how to deploy a benchmark in Addigy, you already know how to use this. This introduces controls for blocking network access to major AI services like ChatGPT, BLOOD, Copilot, Gemini, Brock, Ben AI, Perplexity, and DeepSeek. It switches off AI built into browser tools like Google Chrome, and you could even turn off Apple Intelligence and Siri where policy requires it. AI is a true multiplier for your business, but only when it’s managed and deployed intentionally. Let’s see what this looks like. One of the nice things about this living in our existing compliance benchmarks is that you can easily clone it and only use the controls your organization needs. We hope this could be a great starting point to help you reel in AI in your organization and start taking back control from shadow IT. Today, all of this works while you watch. The goal is an AI that works while you sleep, something that diagnosis, stages a fix, verifies it, and hands you the receipts by morning. While we’re not announcing that today, everything you just saw, the gates, the permission, the audit trail, is how we build up to that future. It may be closer than you think. I wanna end on this screen because this is really the most important takeaway. Everything you saw today, the filters, the scripts, the reports, the MCP server, the benchmark, it sits on top of these five commitments. Your data never trains a model. Our inference runs on enterprise AWS bedrock, and your fleet data stays your fleet data. Nothing changes without a human. You watch that gate fire today in the script assist diff and on every MCP change. The AI cannot exceed the admin. It runs with your exact permissions. There is no super user AI account anywhere inside of Addigy. You can prove what happened. Every AI initiated action lands in your event history, and the worst case is off the table. Device wipe and mass deletion are not gated behind an approval. They simply aren’t there. Anyone can ship AI features. The hard part, the part that matters when it’s your devices, your clients, and your name on the contract, is trusting the AI to handle real work on your behalf. So start today. If AI excites you, start at do it easier in Climb. If AI worries you, start at govern and take control first. All these features will be available to all customers starting today until the end of October. If this is something that you’re interested in, just fill out our poll, and somebody from our team will reach out to you right away. Thank you, and welcome to the Frontier.
The future of AI in Apple Device Management
Now Announcing: Addigy Intelligence Suite
Joel Cedano walks us through the NEW Addigy Intelligence Suite: the intelligence layer inside Apple device management. You describe what you need in plain language, and the platform supplies the Apple and Addigy knowledge to propose the fix. It proposes, you approve, and it executes in real time — nothing touches a Mac without a person saying yes.
Speakers: Catherine Davis, VP Product Management, Addigy
Joel Cedano, Principal Product Manager, Addigy
Welcome again to Addigy Frontier, everyone. I hope everyone here is enjoying the previous session so far. My name is Tim Cruz, VP of customer success at IG, and I am joined by Tim Pearson, CEO and founder of CreativeText. Tim runs CreativeText. He’s an Apple premium technical partner. And couple weeks ago, we were just talking about how he’s been with us since, 2016, if I recall correctly. So he’s been running Apple fleets on this platform for about ten years. Creative Techs works with small and mid sized businesses across professional services, creative, health care, and tech. But Tim will tell you it’s less about the industry and more about the mindset. These are companies where they want their technology just to work for them so they can get back to things that are actually what they’re good at. Now let me go ahead and get ahead of a problem that we’re gonna have here for the next fifty minutes. His name is Tim, and my name is Tim. So we’re gonna do our best here to say Tim Cruz and tear piss Tim Pearson towards each other. Tim, welcome. Thank you. And you can call me Tim Pisson. That’s alright too. I’ll take whatever. Just don’t don’t call me late for drinks. We’re good. It’s all good. Awesome. We’re making this live and fun. I love it. Thank you, Tim. And here’s why I wanted him in the session specifically. It’s not only for the comedic relief like you’re saying, but it’s also, the the technical thought leadership he brings here. He’s gonna tell you what actually he does across his clients, including things that he’s decided not to do and why, the real world application of many of these scenarios, and how to think through it. So one quick note before we start, this session is recorded. It goes out to everyone who’s registered. So if you you do not need to write down any configuration details or anything like that, you can reference the the recordings later. If you have any questions, please drop your questions in the chat as they come up. We will follow-up with them, in in another session, or in some cases, those might turn into formally pseudo talks that we run, almost every every month. Can I can I before we go further, can I just ask a a request to the the everybody out there? If if they pick up something from this where it was like Tim said, don’t use our last names. Just just be Tim said. So when it gets back to Apple, you know, and and one of us would get in trouble, then maybe it’ll be that Tim instead of this Tim. That’d be cool. I’d appreciate it. Love it. Alright. Let’s talk about today’s session here. Four ways to do SSL. Most admins cannot tell them apart sometimes. That’s what we’re gonna be talking about. I wanna be honest about where that came from. It really came from you all. It came from our Addigy teams having really good conversations over and over with our customers like yourself, attending front, Addigy Frontiers and beyond that as well. Somebody asked about SSO. In twenty minutes, it became crystal clear to us that both people have been using the word SSO to mean four different ways sometimes. And their use cases are supported in most cases, but which SSO do we use, and what are the benefits? That’s what we’re gonna be talking about. Apple has a framework and a mode inside their framework, and the mode inside their framework, both are all called SSO. There’s three areas that are called SSO in their framework. And we also have a product called Addigy Identity and a separate feature called enrollment SSO, which is part of that framework I was referring to as well. They all sound the same. This but they all solve generally different problems. So here’s the deal for the next fifty minutes or so. You’ll know which solution fits your environment. You will know which one’s ruled out and why. And Tim Pearson is gonna tell you his success stories and also his opinions of them all. Now if you still leave unsure, I I will hand you a tool at the end that narrows it about narrows your choices down in about two minutes as well, so that’s something you’ll take away from this. So sorry. Can I ask a a stupid question? This is this is the fun part. Okay. Good. Yeah. So so when you say SSO, though, so is SSO so, I mean, I I get the single sign on, but are we talking about just to get into the device, or are we talking about more than that? It’s a great question. I I think it’s, you know, one SSO is one ID identity, one signal one sign in. My apologies. Not signal. One sign in. But your options of getting into the device to your your point, Tim, is one option. Or when you’re already in the device, what does that look like as well? And we’re gonna talk about that too. But, before we jump into that a bit, like, let’s just level set to where Tim Pearson was going. Like, what what is SSL overall and what it actually does at a high level before break it down into four buckets. And that is one identity, one sign in. Like, that’s what we’re talking about here. We want to, at the highest level and you actually, we want you all to have the tools at the highest level to authenticate once against your identity provider instead of managing a separate password for every single interaction app, device, service, so on and so forth. Right? And that’s what Tim Pearson is alluding to. What this solves at the highest level, password fatigue, phishing risk. You know, you’re you’re not trying to remember, like, 40 different devices I mean, 40 different passwords as one user. Onboarding friction, it’s like, oh, do I use this password here, do I use the other password? And the help desk tickets, ideally, that come in from Juggenic credentials across the fleet should go naturally down if you’re doing this right. So, that’s what we’re we’re gonna be talking about here. We when we talk about SSO, we want one user identity as a source of truth that we can land on, and we want your experience, your users can trust, and one that you can control, and you have that confidence you control control. Alright. Let’s put all four on the table. Well, I think we all know what SSO is at a high level, but let’s really talk about where the confusion lies. One framing that, that helps before I do. Three of these are Apple’s frameworks, and I’ll call those out real quick. And one is ours that we built, from the ground up. All of them are included in your current Addigy subscription, so let’s get started. So the four options we have here, and we are going to break down each one, there’s enrollment SSO. Think of this as the quick Addigy check-in that makes the user sign in with their work account before a new device is enrolled right out of the box. Platform SSO, this is the Apple’s built in way to log in to the Mac itself with your, IDP credentials so that one sign in just to unlock the device overall on a reoccurring basis every day, every week, however that works. Extensible SSO. This is the Apple underlying SSO framework that carries one sign in login into apps and browsers. So think of it as you log in, through your browser into your Microsoft, 365 account that extends into the native apps that on the Mac OS level as well, so you don’t have to log in twice into this exact same resource. And then Addigy identity. This is the custom login window that we have developed at Addigy that signs in users with your with their work IDP. It creates the local Mac account, just in time login, and gives them a see seamless experience. It also makes it brandable as well so they know this is coming from you. So let’s dive into the first one here. And the way I wanna this is gonna work for over the next few slides here is that I’m gonna explain one in-depth, and then I’m gonna ask Tim Pearson, hey. What’s your opinion on this one? Right? So the very first one here is enrollment SSO, and this is the one people most often misunderstand or just don’t fully understand, you know, what the use case are here overall and what it is. And what this is is specifically a checkpoint. Think of this this as just purely a checkpoint. During automated device enrollment, before the device is allowed into Addigy, the user authenticates against your IDP. Where this lives is setup assistant during ADE right after two terms and condition. And when this appears is just once, so you’re only gonna see enrollment SSO just once during the life cycle of the device. Sometimes that’s the misunderstanding here overall, and that’s that’s the part that I wanna call out. It’s the gate, not the daily login. That’s the way you think about it. If you expect users to see this every morning, you probably pick the wrong, SSO component, and we’ll talk about the right one, in over the next few slides. What it closes, or what’s really what’s what’s the the risk that this closes overall? Anybody who opens the box can enroll it enrollment gap. Basically, what you don’t want to happen here is that a MacBook Pro is shipped to somebody. It’s stolen by a malicious actor on the way to their to where it’s gonna go. The malicious actor opens up the laptop. They’re enrolling it, and they’re seeing all your corporate assets overall because the the zero touch process is flowing. Now with enrollment SSO, only the users assigned to the to that device and the IDP can complete their enrollment. Meaning that if that bad actor tries to open it up, they can’t enroll the process because they need the credentials from the user that it was going to be assigned to to actually continue the enrollment process. That’s where it’s critical there. So IDPs that it’s supported on, Okta, Google Workspace, Entra, or any Samuel IDP, the broadest IDP support by the four by a wide margin as we go through the four options here overall. It does work on iPhone and iPad, not just Mac. Not every vendor does a login window on mobile, so just keep an eye out on that. And what this needs specifically from you, well, just automated device enrollment configured plus the Samuel app with, like, the identity ID, ACS URL, cert map, and users assigned. Do not use this if your devices are not going through ADE. It just it just won’t work. Just won’t do anything. That’s the prerequisite. It is super important that using automated device enrollment for this. This is the zero touch workflow where you’re sending it to your the user that’s gonna be using it. They’re opening it up, and they’re logging in. And the most the bonus that most people miss, paired with end user directory sync, which we might briefly talk about later on, and the device auto maps to a human in Addigy so that all those configurations and settings automatically apply, assuming you don’t use Addigy identity, but more to come on that later. Tim, I’ll point it to you, Tim Pearson. Are you gating enrollment today? Are you handling in another way? What’s your opinion on this overall? We we’re not. We I can see the use case. We definitely have customers where, like, the security concern would be the reason to drive to this, and we’ve talked it through with those customers, and they’re like, So I’m not saying it’s not important. I think it is, and I think that they’re they’re a 100% use cases. I prefer some of the other methods for for the teams that we work with. And and and I’ll be fair, in the first three times I tried to make this work, it didn’t. And so that was that was another that’s another issue. But, yeah, I I I do think I think it works now, but we just haven’t had the opportunity now to go back and try it with somebody. Yeah. No. That’s totally fair. And and honestly, based off past conversations you and I had, I believe, like, part of your value add is also, you know, getting those devices and truly making sure it is set up too. So for those people who are choosing not to just ship it directly to the end user, they want to make sure that everything is configured correctly. Like, it’s right there for them to then sign in. That’s something that you personally do from past conversations. Is that fair to say? Sometimes. It it all it all depends. And and I do think that this this would if that was your if that is your 100% workflow, that that would get in the way. I love and and we’ll talk about it later in the day, but I do love to, like, have app Apple send that box to the end user and have them open it up and just, you know, we’ve never touched it, and they get on they get on the Wi Fi and click and go is is a fantastic experience. We’re not using an enrollment SSO for it, but I I love that. The less I can do the less I have to do The better. Yeah. The better. Yeah. This is what it does look like when they get to the the remote management screen or when they get through that process. You they do have to put in their password to make sure it goes through. And for those who don’t know, like, we’re actually putting QR codes on the top right hand corner of the screen. So if you’re looking for the setup guides on this, more than happy to just go ahead and take a snapshot on that, or we will also provide this after as well. So if you miss this during the session, perfectly fine. This is something that, we’re letting you all know in each, specific slide. Alright. The second one. This one is getting a lot of attention right now, platform SSO. I’ll walk you through what it is and why it matters and all that fun stuff. So what it is, this is Apple’s own mode inside of the extensible, SSL framework that ties macOS login itself to your IDP. It’s not a web view. It’s it’s not a the login window custom. This is actually the native Apple login window in itself, specifically for macOS. Why this matters? One IDP identity drives the whole Mac and its app experience. Password sync optional, password less through the, secure enclave setup, and this is what it finally will eventually replace active directory binding for those who are very familiar with that process, from from way back when. Where this shows up, login window, firewall, lock screen, native apps and browsers, and we’ll talk a little bit more about the native apps and browsers in the extensible SSO section. And when you see this, while you see a registration prompt or a setup assist on Mac OS 26 and above, it calls out the setup assist part that was the single biggest adoption component of this overall for a lot of teams. Now it’s gone, in the latest operating systems, and I will show you a quick video of what that looks like shortly. Idp supported, Entre ID, and Okta natively, and that is the list. It it’s it’s really Entre ID and Okta. What this needs is, Apple Silicon, or if you are in an Intel Mac still with Touch ID, and it which, only supports in certain cases, I’ll I’ll jump in shortly on an MDM with an extensible SSO config and the IDPs own platform SSO extension apps. Let me just be very clear in what I mean by that. For Entra and Okta natively for it to be supported, you need a third party app from them, which we we have in the setup guide of what you need on the machine for it to work. So that is a requirement. Do not use if your IDP is Google or another one that I didn’t mention outside of Okta or Entre at the time of recording. You that that those are not at this time through that framework. You do need MFA in sourced, enforced. Excuse me. You do need MFA multifactor authentication enforced at the OS login window. Or if you are an Intel Mac, with Okta, do not use with Okta because the Okta is a third party app I alluded to. It’s built only for app Apple Silicon support. So you you would just run into to issues with that overall. Overall, this is the long story short, in my opinion, platform SSO is still maturing. We we see where Apple is going with this. This is something that they’re evolving with every single year. It’s still a little early, but it is moving fast. And one small change in that is extensible SSO, like, as you’re using it can have, you know, some positive or some challenging effects overall. So here’s how I would personally approach it when it comes to platform SSO, especially for those who’ve never used it before. Separate policy and Addigy, test device in there, not production. You’re able to do that. Test on latest Mac OS major updates because it does have an impact how platform SSO works. The latest the the Mac OS update, which is right now Mac OS 26, the better. At least that’s live in production Mac OS 26, so you can see how platform SSO works for you in your environment. This is where I’ll hand it over to Tim. Tim, I I think you have some opinions on platform SSO from what we talked about in the past. Where do you land on with platform SSO? What are your thoughts on it overall? I think it’ll be better next fall. I mean, I I love the dream state. I think it honestly, like, it it’s it’s where I think a lot of things should be headed to, and I think, you know but I also think that we’ve I’ve been in a few special trainings with some special fruit companies where they were telling us how great this is, and we couldn’t get it to function. And so I think that that’s changed now. I think that it’s you know, I don’t I think that it’ll be better in Mac OS 27. I think that as a solution, if I was if I was in house and was hand you know, doing one company, I think it would be it I would be working **** ** getting this rolling. If I was if I was a, you know, an MSP type business where I was managing twenty, thirty, 75 different companies, I’d probably be holding off on platform SSO at the moment. Do can I ask you a question about this, Tim? Yeah. Please. You know, my memory is fuzzy sometimes. Do either of these two SSOs require managed Apple IDs? They don’t on these Okay. Particularly. So they don’t require managed Apple IDs. That’s something that That keeps the lift lower. Right? That’s correct. That’s correct. And, you know, just kinda tying it back to conversations we had offline, you know, it’s definitely, I I’ve been in in your shoes, and we’ve had either one off, not one off. We we’ve had meetings around platform SSO overall, you and I. And then it’s also there are other customers too. Right? And I think how you were describing it was actually very clear and and correct, like, you know, depending on your use case and maybe if you’re just a one shop, one one per particular thing. Because I on the reverse side of things, I have seen positive they’re small, but they’re positive impacts the platform SSO and how those workflows work. You you just get the dream state of around passwordless. Like, I’ve seen people have pass the as it working, and they’re putting their finger on on the biometrics, and it just bam. It works. Just logged in, right Yeah. After things are set up. So it it really just lands on this honest answer that I think both of us are are aligned with is the the honest answer is it depends on the shape of your fleet Yep. And more than whether you know, if not the technology is good, it’s like what IDP you’re using, what your use cases are, and you’re gonna see either the positive benefit of it, or this is the no, not now option. Like Yep. Right. See you next swell type of thing. So that I think both are really good. In my world, we are doing more and more shared devices. Is platform SSO gonna work with a like, if like, a shift workers where different people are coming in and using the device, that’s not gonna work in this scenario. Right? I I think it’s a great question. I think it’s a it depends answer. I think it depends on if it’s macOS for the current iteration, maybe not. Depends, but maybe maybe not on that. For if you’re sharing devices sharing an iPad, particularly, then I can definitely say no, not platform SSO because you should be using shared iPads. Shared iPad. Right. Right. And that and that is the scenario where I would say DefLink does require federated managed Apple IDs for that, and that’s us selling into Apple Business Manager and being able to do that, which is a completely different use case. But another option there that you can have is if that is a a scenario. Yeah. And I was thinking more like retail type environment where they’ve got maybe a couple of iMacs at a front desk or, like, a doctor’s office or something like that where there’s there’s people, but those people maybe are changing throughout the day and the shift work Yeah. Part of that? Platform SSO isn’t really gonna work for that, is it? No. But I’ve definitely seen shared iPads work on that for sure. So I’ll I’ll share yeah. I’ll share one you know, in retail, definitely, we we do have a retail use case here where, I’ve seen them on the field that it’s just one iPad to five shift workers, for example, and, you know, they’re just in rotation. The five are in rotation. They’re not being used at the exact same same time, of course, but they’re able to log in, and then they get into their POS system at the time so they know who’s logging in, and then they’re gonna be able to execute things up there as well. So that’s something that I definitely see. So, yeah, really good. Alright. The next one I wanna get into here is, this video. For those who going back to a platform SSL and just haven’t seen it work in some way, I just wanna do a short video of what that looks like. So this is a device that’s already ran through automated device enrollment. So this is already enrolled into Addigy. This is what the user Steve at the desktop level. It is a native registration notification and then prompt that you’re seeing here, and they’re putting in their credentials at yours as you’re seeing. So they put in the password here. It will be asking for their MFA code, for example. So this is putting from Okta Verify in this case. You’re putting in their their number, their their MFA code. And then it just really it’s a guided prompt. It’s a seamless guided prompt that they’re seeing the end user on their side, and they’re being they’re able to log in, overall. So this, allows the password sync to happen behind the scene. The account is actually getting bound to the local Mac account there. And then you can check to see if it works by actually going here, and you’re gonna see this green dot right there at the user level to really validate that, yes, the user synced and locked in through Okta Verify in this case. And Okta Verify was that that third party app I mentioned in the scenario where you do need to install on the machine for it to work. And, of course, for the Microsoft side of the house, that’ll be, the the the company app, that Microsoft provides as well as you’re able to use that. Alright. Moving on to the next one here, the extensible SSO, the third one here. This is the least talk about of the four. I’m just gonna be transparent on this one, of course. And I understand why because it while it does have powerful application, it’s, in my opinion, very niche in its use case. And not to confuse the audience, platform SSO is a subcomponent of extensible SSO. And for this section specifically, I’m not talking about, I’m sorry. I am talking about everything in extensible SSO that is not platform SSO. So pretend like we’re not talking about platform SSO here. That’s the takeaway. So what this is, this is Apple’s foundational framework overall and how they’re trying to extend into IDP using IDP credentials to the macOS framework or their overall ecosystem. And IDP extends, extension plugs into the OS and carries one authentication across apps and browsers. That’s the dream state. The relationship here, particularly, SSO is a mode inside it. Like I mentioned earlier, if you run platform SSO, you already are technically using extensible SSO on the device. Why run this on its own? Well, it’s low commitment entry point. For those who are trying to, you know, test the waters as to what Apple is doing, this is a low entry, to do that. This allows you to log in through a native app like Office three sixty five and then extend the SSO component to the browser side of the house as well. So if you have cloud apps that are utilizing the same credentials, you don’t have to log in again there. It just extends through the browser or vice versa where you log in through the website and then it extends to the apps without ever touching the login screen again after that. So there’s nothing at risk here. Just to be very clear, it’s getting your feet wet on the SSO ecosystem of Apple and just getting an an understanding on things. It does not change the login, window for macOS specifically if you just focus on the extensible SSO part. Where this lives, native apps and browsers, like I mentioned, the IDPs that support this today, Entra and others through a redirect, Kerbois and Active Directory through credentials. The credential type is the bridge that you’re still running AD alongside the cloud app as well. Just wanna, let you all know about that. When is this needed? Mdm plus an IDP SSO extension, one payload per device per extension per domain. So a little bit a nuance there, but this if you want a little bit more on that, the setup guide goes in deep on it. Not not as complicated as probably how I’m returning it. Do not use this if you need the login window, if you’re trying to modify FileVault in some way, if you need a password sync or password less option with your local, login. That’s platform SSO, which, again, that’s a subcomponent of it, but not specific for this conversation. And here’s the caveat, to put on the table before anybody deploys this. Extensible SSO works out of the box with Safari and with macOS apps that support SSO. Other browsers are profitable but requires additional configuration. So the Chrome, so the Firefox of the world need additional configurations to participate in that. And if your users live in Chrome, you need to plan for that work rather than assume it just comes you know, it just works right out of the box if you just play it. So that’s what I wanted to call out. Tim Pearson, general thoughts on Extensible SSO and its use cases overall? I I actually, a couple hours ago, was talking after you and I talked last week when we were just kind of reviewing what we’re gonna do here today, I brought this up to a customer today. I was like, what if we could do this? And he was like, he loved it. He thought it was a great idea. I, of course, have now more questions because we’re not using this, and, you know, we’re probably not going be able to. Because one of the things that I was going to ask so you can’t some of these solutions, it almost would be great if you could kind of, like, layer them on top of each other. You know what mean? Right? But you can’t, can you? Like, I can’t do the the the the first SSO we were talking about where it happens at, you know, preenrollment Yeah. And then still roll in extensible later. Right? I it’s it’s one or the other. Actually, I so I’m I’m gonna contradict something I’m gonna talk about later, but, you know, it slightly contradict. Not a lot. But I think you can layer in, but I don’t think you can use all four. That’s the way I I I was gonna share later on. Like, it just depending on how the experience is, I think you can layer in. Like, so for example, you know, just to jump ahead a little bit, I think you can have the enrollment gate with enrollment SSO. That is one login, but you’re not gonna extend that one login to everything else. But after that, you can just say, look. That was just for a security gate process. Now this is your true login. And then you can riff on platform SSO and and extensible SSO. So, yes, those two things can be combined in in very niche, scenarios that I have seen work, but I won’t discuss here. For those who are interested, I I can talk to you all about it off of this session. I’ve seen actually people utilize, platform SSO and Addigy identity on the same machines as well. And there is a scenario for that as well, but we won’t get into that today. So I to to your point, Tim Pearson, yeah, I think that you can layer it in. It’s just a matter of, like, what the use cases are. I don’t think you can layer all four collectively. I think there’s there’s gonna be it. But two is good to to layer in. No more than three is kind of my general thoughts around that. Okay. Cool. No. That’s that’s great. Yeah. Because as I was watching I was I was thinking, and I was thinking ahead to identity, which you’re probably gonna talk about next. I don’t maybe. Yeah. No. It’s it is the next one. It’s like you knew. So the fourth one is is our the Addigy identity. And and, Tim, I Pearson, I would love your your thoughts on this one. But just before your thoughts, I wanna jump in what it is. And it’s a macOS login window replacement that we developed in house. It signs in the user with their work IDV account, creates the local Mac account just in time on the first login. So why does this matter? Well, it’s the order people actually care about. Just in time account creation, why they get device right out of the box. Nobody’s pre nobody has these prestaged accounts. They’re just built on the fly. IDP password sync, so the login was, the local password Stops Drifting. MA MFA through their IDP, emergency offline bypass so you’re not locked out when the Internet is, especially for those who might be on an airplane that the Wi Fi doesn’t work so well. There is a bypass that they can do, a safe and secure bypass that they can do so that they can log in without Internet connection. Zero touch install, and it supports Google. Native platform SSO does not. That was one of the things we called out at this time, does not support it. So if you are a Google Workspace shop, this is your answer today. So where this lives, the macOS login, like I mentioned, what you need, an Addigy account, with identity enabled, a supported IDP, and an Addigy policy, minutes to set up. Do not use this if you, constantly log in to active portals or public Wi Fi at login. There’s a workflow for that, but it there is some there’s a little bit of friction on that. You need an offline MFA workflow for that. So, like, the authenticator apps are perfect for this. Or if you want Touch ID at the login window, that’s gonna be platform SSO that that at this time. So macOS only to be very clear. So is that something you can deploy on a on a iPhone or an iPad? So, Tim, I’ll I’ll throw it back to you. But, you know, there you lean pretty heavily on this today. You know? We do. We we push you across one ear, but why? Well, I mean, for all the reasons that we should love, like, a managed type of login. Right? So, like, it just the the identity side of it, I think, is huge that, you know, we can we can tie the user’s login to their Google account or or you know? And and we’re keep that, you know, one less password that they have to manage. We know that the device is secure. We also know that, like, it makes onboarding and offboarding so much easier, and we tend to do a lot of onboarding and offboarding for end users with some of our customers. Others, they only onboard. They’re amazing. Whatever. But, you know, I think that there’s there’s a lot of that, and so I love it. I love that from a support standpoint from my team, it’s the same experience. So, you know, users, even if they’re on if they’re a Google shop, you know, we support businesses where they are. So if they come to us near a Google shop or they come to us near a Microsoft shop, we’re gonna support them wherever they are. Right? And so to be able to take that and then tie that in and and have the same experience for those users or, you know, very similar experience is is key for us to be able to support at scale. So I think I I love it. I I like the idea of so I you know, when we were talking, I was like, I really like the idea of doing this plus the the extensible SSO. Yeah. If I if I could do that, you know, like, that seems like a a pretty good solution for people. And, of course, test, test, test. But, yeah, I’m a big fan. We’ve been running on the identity bandwagon for several years now, and, yeah, love it. Really do. Yeah. And just recently, like, we we made some major changes a couple months ago, especially around, you know, just to call out one of many that we did, the silent silent fall vault unlock. Right? You know? And you and I talked about that before. Like, you’ve had the silent fall vault unlock running in production for some time. You know, what what did that do to your clients or use your ticket volume, right, overall? Like, how how’s that experience? It’s cut it by a lot. I mean, there’s still I I you know, we still have the training that needs to go into end users because, you know, we have a lot of customers who, frankly, have contracts with companies like Microsoft that require in their contracts that they re they change passwords every ninety days, which is exactly a 100% opposite of what Microsoft’s act actually actual guidance is. Right? But but if you’re a vendor for them and you get the big document from their purchasing department, that’s what it says. It says, we’re gonna do this and we’re gonna do that. And so, you know, for our customers, a lot of times that are that are on this and and, you know, of course, you also have to have FileVault enabled. And so that password change every 90, and then the user doesn’t log out, and they don’t log back in, and that that you know, they they’re Mac users. Mac users never have to restart their computers, and so, you know, they change they make a password change and forget what the old password was because it’s been thirty days. Yeah. And so that that was one of our biggest tickets was just that, and I think that new change has has reduced the ticket count quite a bit. And it’s it’s it makes my mornings a lot easier because, you know, it’s always that Monday morning rush. Oh, I changed my password two months I just restarted. I got back from vacay I did it when I went on vacation, you know. And so, yeah, I I I love that feature is is is a big one. Love it. And another one another one that I’m excited about too that I haven’t gotten to use yet, but I think that we can assign end users to the device or there’s some there’s more about that. Right? Yeah. And and, you know, it does connect very well with Addigy Identity. So for those who don’t know, we we relaunched a or released a new feature a few months ago. It’s a end user directory. You log in, you’re gonna see it on the left hand side on your in your in your menu bar. And that also can be driven by Addigy. So you can actually set up a SCIM server, those users. You can preload them into Addigy. And, you know, for many of us, here, when you’re onboarding a new user, you know well in advance that they’re coming on. And then you set them up in your IDP, but you just keep the account disabled. Right? So to kinda give a scenario here, let’s say September 1, you know that somebody’s gonna start working at your company in October 1. Right? You can preload them. You can set them up. And then come, October 1, before they even log in to Addigy identity, the device is already assigned to them. It automatically goes to your workflows. You’ve already set up an Addigy. You just don’t have to, like, do it live at the time there. You’ve done it preemptively, and and that’s what Tim is referring to there. So the end user directory, assignment seamlessly connects also to Addigy identity so that after they log in through Addigy identity, it’s like the final check again, and you’d just interconnected there as well through a lot of the automations that you’ve you’ve set up in Addigy. So really cool call out there as well. So you could use that then to, like, set policies and stuff too for like, is that possible? Absolutely. Am just now am I just making it up that you guys gotta build? No. That is possible through flex policies or auto assignment, however, with the the you you, you called it out because I know those two terminologies are in the Addigy world as well, so that that works out. Alright. For those who don’t know what, it it what Addigy identity looks like, I just wanna throw this out there. This is another quick demo of what that looks like. They log in. This is, again, replacing the login window here, so they’re not inside the desktop yet. They’re logging in. They’re putting in their, two FA. This is what we’re referring to as an offline one. You can use this, or you can use Google Authenticator as well as in this example of Google. And then you log in. Notice there’s no double log log in, no nothing. You’re just right in into the gate. So that’s that’s really as simple as that. From the field. So, Tim, this is where we get to talk a little bit more, about it, but you’ve shared a lot of really cool stories already as we’ve gone through this. So this one might be a shorter version in itself. And those are the four types of SSO we talked about, what each option’s for, what they do. Now I want you to talk about this if you don’t mind. Like, I this is a quote that you told us actually, and it comes from a story that you had from one of your clients. Why don’t you tell us who this is, what happened, and share that story with us today, if you don’t mind? Yeah. Sure. So we’ve got we manage for this particular customer, we manage about a 100 devices within a sea of Windows devices. You know, there’s four or 500 Windows devices. There’s eight guys managing the Windows side of the house. And the CEO from this company who who is a you know, started as, a graphic designer. He’s an ad he’s an ad man. And and I think now is is is a good friend. We’ve known each other for probably ten years. He hadn’t had a new so the way we we do identity, lot of times, is we’ll add it to we’ll put it in a flex policy, and if somebody changes a device or something, then they’ll get you know, they get a new device, and then they start the identity experience. Well, he actually hadn’t had, a device with identity yet. And so what was really cool was he got his new device, and the, you know, the IT team was kind of freaking out on me, and they’re like, Hey, you know, we, like, we can’t screw it up with Andy. I’m like, Don’t worry about it. It’s cool. Just give him the box and send him home. And and he was like, I you know, they were like, No, but it’s got and I said, Just give him the box and send it home. He knows how to get in touch with me. We’re cool. And so they did, and they they gave him the box. They told him to just open it up and log in. And I think your next slide is is the the the quote that I screenshotted and sent it over to him. And this was and then I, you know, I forwarded this to you guys’ team, but this is this is exactly what he said to me, you know? And and and he was right. So what had happened was he opens the box, he gets it on his Wi Fi, and and then, he gets the identity screen, you know, and and for the well, we’ve customized our identity screen a little bit, they get, like, the company background and they have a company logo on it, they know that it’s them, and it’s got and it’s got his Microsoft login right in front of it. And, you know, he logs in. It gets set up. You know? And he oh oh, and then the the next part of it too is assist launched. He’d never seen assist before. And so he gets in, assist launches. Boom, boom, boom, boom. Here’s all his apps. You know? Hey, Andy, your device is set up. Let’s go. And it was it was a huge win. It was fantastic. And and the honest truth is we’ve been doing this for a couple years for his team, you know, and we, you know, and I had to do nothing at this point. Right? Because we we’ve got it all set up. It’s all it’s all fired. All I had to know was just what policy his device needed to get into so that he got the appropriate apps, it’s great. And so, yeah, it it it’s things like this, the those types of touches, I think, that make it so that, you know, a customer’s not gonna leave us. Right? And I think that when you’re when you’re guys doing what we do, that’s you know, customer retention is really important, and this helps drive that. So, anyway, yeah, it was a great experience. A 100%. Thank you for sharing that, Tim. That’s an amazing success story there. And speaking of success stories, you know, this is the section, you know, we talked about platform SSO. We talked about extensible SSO, enrollment SSO, Addigy Identity. You just shared a really cool story with, like, how Addigy Identity is impacting one of your clients, a key one, for past conversations. Just from your opinion and the use cases you see, which one of these four are you highly recommending? Which ones you’re keeping an eye on, for future use cases? You know, what’s your overall opinion as to the state of SSO capabilities when it comes to managing Apple fleet? I mean, I think the platform SSO is where a lot of stuff is gonna go. Right? I I think that that’s probably where a lot of things are gonna end up for Max. But for us, we lean on identity pretty heavily. We we lean on ad Addigy identity fairly heavily, and I think there’s a there’s a bunch of reasons. One is because, you know, I was asking you about it earlier. We run into a lot of those scenarios where there’s maybe a shared device, you know, where it’s it’s maybe in a print shop, and there’s two shifts, but they’re running the same Mac studio. You know? And so to have be able to have those people come come in and switch out and, you know, all the stuff’s still there. You know, they’re not going buy a studio for every employee. That’d be silly. And so, you know, stuff like that, stuff like where, you know, retail or health care, you know, where the there’s people switching out devices a lot, I still think that in a shared environment that that probably Addigy identity is gonna be the winner for us. You know, I think we just talked earlier about some of the some of these are are great or or have potential to be great. I haven’t I haven’t personally been able to necessarily make them all work the way that I wanted to make them work in a way that was comfortable for me to roll out to a customer. But I think that that’s changing, and I think that it’s getting better. And and I’m I think that, you know, come October, late October after, you know, we get to twenty seven dot two, it’s time to, you know, probably take another look at look at these again. Right? And this is like this that’s the time when we need to look at our identity tools and see, alright. Can we go? Can we you know, where do we make these moves? That’s that’s my gut. But you know? Yeah. No. I and and you and I talked about this a lot, and I, you know, you know, agree agree with your opinion and thought here. And, you know, one one of the commencement commitments we’ve shared with our our customers and is that, look, you know, as as Apple launches new capabilities, we’re gonna be in the front lines, implementing it and giving it to you all as well. So I do agree with the sentiment, like, where Apple is going. That’s where the the the hockey stick or hockey puck is going to a degree, and, we’re we’re quickly and iterating iteratively keeping up to date on that. And that’s something I think I agree. Like, it come next year come come even October time frame, right around the corner next year and beyond, you’re gonna see major changes on that overall. Alright. This is one yeah. I mean, if if you see that’s where they’re going, go follow them because one day, they’re just gonna shut off whatever you wanted. So don’t fight. Don’t fight Apple. And one thing I I will call out to that point as well, like, they they live off of Apple feedback. For those who don’t know, and we’ll we’ll probably have a maybe a pseudo talk on this or if we we have one already. The Appleseed, program, Apple feedbacks, they live, eat, breathe that. So if you have some strong opinions as to where things should go, like, that is the Apple preferred way as to how you bring those things in. One thing I wanna call out because I I, personally, I I love bringing some level of success stories here that are are real and out in the field. I did allude to this in the past, but there is one, company that I was thinking through, that, you know, they are in the technology and software space. They manage about a thousand devices, a little under a thousand devices. Most of them are Mac. I think 80% of them is about Mac. Their I the IT director to software and technology company, they mandate Safari across the whole organization if you’re on a Mac, which is, an interesting, thought there and and supported, to be clear. And then they also mandate Microsoft Office three sixty five, and they’ve had huge, huge success in using extensible SSO, without even the platform side to be cleared, platform SSO side because they pile they have a a lot of custom cloud apps that take the same login, and taking away extra clicks in the day to day workflows of their end users is massive for them. So I just wanted to bring that up. I I know this is not a heavily used feature across the board, but there is strong success there overall, and it goes back to that theme. It just it depends on your use cases. We wanna give you the tools in your toolkit out there as to what might be best depending on the scenario, so that way you come out as a rock star knowing how you can resolve each use case that comes about. I mean, I I love I wish as as someone who’s worried who’s, you know, security keeps them up at night, you know, and the security of my customers and stuff, I wish so badly I could get Chrome out of my life and, you know, and not have to manage those updates every single day be you know? And and I know that it’s much better with prebuilt apps, but it also feels like we’re still you know, that that’s not really the problem. The problem is that that software is a struggle bunny sometimes. And Yeah. I know people I know people love Chrome, and I you know, customers ask me, and I’m always like, hey. If we could just turn it off, I’d I’d be fine with that. And maybe this maybe this will help me move a few customers in that direction because, you know and I probably take a lot of heat for saying this. I it’s probably in the chat right now. There’s, like, arrows coming my way, but where is school? That’s totally fine here. And and that’s a good segue to talk about the gotchas here as Luca, what you’re alluding to here. Like, what are the gotchas? I’ll give you mine on the SSO side, and, Tim, I would love to hear your gotchas. You and you already been, like, layering them in as time goes on here, but here’s mine real rapid fire real quick as we’re getting short on time. Extensible SSO is Safari supported right out of the box. Rome needs work to configure it, plan for it. There is a use case area to be clear. Platform SSO on Intel, I mentioned earlier, doesn’t work with Okta, so don’t use it there. Okta’s extension is Apple Silicon only. That’s a that’s a hardware limitation, not a configuration one on that one. Plus, you know, there’s some layers of just in time. There’ll but few other things as well on the platform SSO side that, you know, it it’s getting there. Just in current state today, you just need to look at. Addigy identity. Captive portal Wi Fi does not work well with it. Just to call out, that. So if they’re at the hotel or login window, it’s gonna be a different workflow. So there are ways to do it, but you’re gonna have to log in in a different way for the to do that, and there are there’s documentation on how that works as well so you can get to your end users. And the big one that I kinda was alluding to before, my strong recommendation and just as personal opinion, don’t stack all four. I do think you can stack multiple ones here, the SSO options, but I don’t think all four and that’s not the that’s not the the point of this session here. It’s not to say use all four all at the same time. That’s just giving you the tools in your toolkit. There are a couple that stack together and complement each other. The instinct is sometimes to layer off four, but doesn’t work that way. Pick the ones that fit and rule out the others on purpose. It is a okay if you don’t adopt all four here. Tim Pearson, what’s another gotcha you have an experience on here and your thoughts? I mean, FireVault’s the one. I I you know, I mean, FireVault FireVault is something that just you just have to consider it and and whatever. I think in in and to your point with identity, those people who are travelers, you know, those end users who are travelers are gonna have that different workflow are also you know, you’re gonna find out about them once, and you’re gonna take care of them, and then they’re gonna be okay. So I again, like, I kinda like identity because you have you have these things, and and it can you can bring there there’s a lot fewer issues with, like, is it gonna work at this and this and this and this? You know, I I feel like it’s a little bit of broader solution. So I’m I’m a big fan, but, yeah, watch out for watch out for FileVault. I could go on for days, but fewer days now. It works better, but watch out for FileVault. Yeah. I mean, I think I I think that’s that’s really the biggest gotcha. Test. Test. Test. Test. Don’t don’t deploy it to a 100 devices without trying. Yeah. But yeah. But that’s a fundamental IT truth. Sorry. I I do wanna comment out that test test test. That’s too fundamental, for those in the IT world. All of us are in the IT world here. A fundamental truth in itself. We we have some we have some users that are doing we’re doing identity we’re doing Addigy identity with some users that are in Tbilisi, and I don’t know exactly where Tbilisi is, but I know it’s not on the West Coast. But it’s not near me. It’s not in my time zone. And I tell you the first time that we did, we, you know, we sent one of those people a device, and, you know, we had tested and we had tested. But, you know, we were really hopeful, and it worked, and everything worked, and it was fantastic. But I still was a little nervous. I still it was still a sleepless night. But, you know, you gotta test that **** everywhere and Yep. Make sure it’s gonna work. Yeah. Makes sense. Alright. As we’re wrapping up here, I said in the beginning of the session, if you’re unsure of what path you should go down, we made it simple for you. I I promised you I was gonna, give you something, and here here it is. Addigy.com, best Apple SSO solution tool. Addigy.com, best Apple SSO solution tool. You’ll see the link on your screen. We can pass this out to you, later on as well. Two ways into that workflow, you start with your problem or you start with your setup and fleet. It gives you the best fit fit of which SSO solution you need, what else to consider and useful part, what it’s explicitly not a fit given what you told it to. So we’ll call up things you don’t need to use. It’s free. It’s not gated. Run it as many times as you want. Bookmark it. It is yours to utilize. Also, if you don’t see your use case there or you need further details, please tell us in the chat or email us product dot addigy dot com as we will love to review your feedback further. Some of that feedback could be in our product overall, or it could just be in the calculator or future pseudo talk that we run regularly overall. So your feedback matters. It, informs a lot of the content and the information we provide to you and even the product direction as well. And with that, I was wondering as we wrap up here, two quick things. Tim is back with us today for the zero touch at scale session, and identity is one of the pieces that decides whether your deployment is actually zero touch or whether somebody starts to put their hands on it. So if that’s if this session would be useful for you, that one is gonna be the natural one that I highly recommend to you to go to in about the next hour. And second, Tim Pearson, huge thank you to you. Seriously, thanks for giving the people the real experience and thoughts from a technical thought leader here that you are. We greatly appreciate your time and, the comedic hour you kinda gave us in some cases as well. And for everybody here, enjoy the rest of Addigy Frontier, everyone. Take care, and we’ll catch you in the next session.
Identity & Access:
The Missing Layer in Apple Management
Identity is where most Apple fleets quietly leak — local accounts drifting from your IdP, password sprawl, and a login experience users tolerate rather than trust. This session covers what Addigy Identity is, what’s changed (with a live demo), and a practitioner’s unvarnished take on Platform SSO and the real mix of identity options for Apple today.
Speakers: Tim Pearson, Founder & CEO, CreativeTechs
Tim Cruz, VP of Customer Success, Addigy
Zero-Touch at Scale:
From Unboxing to Managed in Under 10 Minutes
A government IT lead managing 3,500+ iOS devices, and two MSPs running Apple across dozens of clients, compare their honest definitions of “zero-touch,” then get diagnostic: the three places deployment actually breaks (the ABM gap, the stubborn last touches, and the humans), each told as a real story with the fix that followed.
Speakers: Monique Hunt, Client Services Supervisor, LouisVille Metro Government, Tim Pearson, Founder & CEO, CreativeTechs
Jeremey Kenney, Technology and Integrations Manager, GlobalMacIT, Angela Diaco, Sr. Product Marketing Manager, Addigy
Welcome everyone to our final session of the day, scripting and automation at scale. So this is a panel with two of some of my favorite people. And we’re gonna talk about automations that MSPs are actually running and what it cost them before it was automated and some maybe even great stories, horror stories to take back to your teams, but just kidding. It’s because we’re preventing those from happening. So here we’ll talk about where automations earn their keep, where they break, and what sort of unsavory things AI might be up to, and what things we wanna make sure that we’re putting in place when we’re testing some of these automations. But with that, we’ll hand it over to our wonderful panel over here, Simon and Ross. I will let the two of you talk a little bit about yourselves, your fleet, and where are you located. Sure. Yeah. Can do. Happy to be here. Ross Matsuda. I’m an Apple systems engineer with an MSP named Antiva, where, you know, my little tagline for these moments is, you know, we manage thousands of Apple devices across hundreds of organizations and dozens of verticals. Personally, I’ve been in the Apple IT space since around two thousand seven, two thousand eight. And I’ve gone from, you know, working at the Genius Bar to doing business to business support, small, medium business, and then moving more from endpoint support and on-site services to administration and engineering. When I’m not doing this, I guess you could call me multidisciplinary. I do a lot of work in in the Chicago community as a a stage director for a couple opera companies around the city here. I also am studying and playing with a group that does traditional Japanese music called Toyoaki Shami san. And so I balance out those sort of extracurriculars with my work with Entiva. Entiva’s a big old honking MSP. We have a what what I consider to be a fairly large Apple install base that is continuing to grow. We love to see that. But even with the size of that install base, is, of course, you know, we’re we’re one cog in a in a much larger machine. And our our dot mix and Windows endpoint client counts are, you know, also very substantial. So we’re handling our you know, the Apple side of the business, making sure our clients are getting, you know, the best service that we can provide and interfacing with technology offerings coming over from from product and then from all of our Windows clients as well. I guess the other thing I should notice in in my little tagline down there is I also author an Apple technology blog called Pseudoaid where I’ll do my best to post, you know, upcoming talks that I’m gonna be presenting in, and just meet things I find, you know, solutions that we roll about, I think, is worth communicating to the community. Alright. Cool. Thank you. And, Simon, tell us a little bit about yourself and your location, which I know, Ross, you you picked up before I asked. And, yeah, tell us a little bit about, yeah, where you’re coming from and about your fleet. Yeah. Thank you, Angela. My name is Simon House. I’m a service delivery manager here at Air IT Group. We’re based in the UK, so over the pond from where you are. My main role is a service delivery manager. I’ve been doing that for two years now, but before that, I was first, second, and third line support working on our service desk. So I’ve had the technical experience in the past with non technical role now, but I still live and breathe Addigy. And one of my jobs as a service delivery manager is trying to bring all these Apple services that we have with our customers and make sure they’re supportable and our service desk can offer the service that our customers need. Yeah. So that’s myself. Thank you. Nice. Thank you. Alright. And I I love that the two of you sort of bring like, what I’m finding is very complimentary views even though you’re looking at things from, two very different seats, very different locations. So I’m hoping that folks here get a lot out of this session because again, we’re gonna be sharing a lot of tools, but then even just I think with all of this, it’s really just about what’s the perspective that’s gonna get us the most efficiency, safety, enjoyment out of this work that continues to evolve in front of our eyes. But we’ll we’ll sort of kick things off with this question about, you know, just generally. I mean, I think it’s good for us to just frame the discussion. How do you think about automation in general at your MSP? And this is, you know, maybe just, I don’t know, just kind of kicking things off. You know, what earns a script? What stays a human decision? How do you make those decisions? And the two of us have had some really interesting conversations here, but it might have even changed in the last, like, maybe month or so that we’ve been, you know, thinking about this session. So I’ll I’ll I’ll kick things off to Ross. Simon, who wants to go first? Yep. Sure. Yeah. Sure. I’ll I’ll get rolling. Automation is automation is life. Automation is how you do more with less, and everybody always wants more for less. And so in in our universe, one of the unique things about or at least to the best of my knowledge, unique things about our our situation at Antiva is that especially when you start scaling inside of an MSP, sometimes the distance between, you know, your your service desk techs and those engineers can get pretty vast between them and and the people who are managing their tools, right, who are actually supporting the platforms that they’re using. But I’m really tight with our Apple team and our our service desk team. And so I I always do my best to stay in touch with them and constantly check-in. You know? What are you getting a lot of questions about? Do you find yourself having to explain certain things multiple times? Or do we have you know, if we go down to metrics, are we receiving a lot of tickets in this specific category? Great. What can we look in there? And so I’m always doing my best to generate automation to free up their time and to increase their standard of care. Right? So instead of, oh, we have this problem where, you know, a service account started losing administrative privileges when it shouldn’t. Okay. Let’s let’s review that. Let’s, you know, write something that can look out for that, take care of it immediately, log it, and and we get on with our day. And so broadly speaking, when it comes to technical automation, I’m leveraging the support desk so that I can give them what they need to feel good about the work they do, to feel that they can dedicate their brainpower and resources to novel questions and novel problems, and to take that repetitive work, and get it out of their hands so don’t have to worry about it. When it comes to a person standpoint, and that’s where I, you know, also ask if they have to explain something frequently, That turns into how we consider automating people, and that’s through documentation. So that’s where, okay, if you’ve had to explain this three or four times to a single organization, let’s make a guide, you know, toss it online, make sure that it’s, you know, easy to follow, easy to access, and then take that load off of them as well. So before we start doing automation, I always ask ask five questions. What can we do? I say, is what we’re trying to do, is it repeatable? Is it is it needs to be done again and again and again? Because, really, we’re all about time saving here, but also we need to look at can the change we need to be made, is it done safely? And if it’s scripted and automated, we can always make sure that is done safely and we can also validate the state afterwards once it’s run. Because we need to make sure what we’ve done has run properly and it’s working. I would just think, yeah, we need to prove has it worked. And then the final question is, yeah, as Ross said, can we support it? There are people in the organization, many of them have never touched a Mac in their life. They work in the Windows machine supporting a Mac user. They got access to Addigy. Well, we have the right documentation saying, hey, you’ve got this problem. This is how you’re gonna go and analyze a problem and this may be your solution and yes, it is. That script, we need to have it documented to say to that person who’s working in the service desk, go and run this script. It should resolve your problem. So, yeah, we always make sure it is supported. And if it’s not supported, then why we’re doing it in the first place? Wow. Nice. I appreciate the both of these perspectives. And it is interesting. You’re right. I know, Ross, you had kind of alluded to this just when we’re at the point of scaling at MSPs, just, like, making sure we’re still maintaining that same line of communication or thread of consciousness throughout different layers that have been put within the organization. But in that frame of reference or even just if we take a step back to just really this very simple question, like what what is that one automation that you feel, oh gosh, this has been sort of like our our golden ticket to just alleviating a little bit more of the strain for folks. And maybe it’s a you know, it saves you the most hours per month, saves you the most tickets, or even just takes that mental load off of you in in a big way. I don’t know. Yeah. Ross, we’ll start with you. And then Simon, if you wanna chime in here too just from your perspective. Yeah. Sure. I think one of our largest ones just comes down to user account management for Macs, and that more specifically dealing with volume ownership and secure tokens. Anyone in the community has come across this. Addigy has created a lot of great features over the years to improve all the built in capabilities as far as secure token detection, remediation. Like, there there’s a lot built in there, and there’s a lot that we’ve built as well. And so one of the major things for us as far as automation has been, we’re always depending on the organization and their risk tolerance, we use scripting accounts, scripting admin credentials that we can deploy to organizations that we can run things against. And to also have as break glass accounts for our primary contacts should something misfire with FileVault. Right? Say, oh, man. We we can’t afford to lose access to this computer right now if something went sideways. We need to make sure that they have some way to get into that computer nondestructively and then that we can keep things secure after the fact. Right? And so we’ve had to build a a series of scripts that we’ve been able to truncate significantly through the use of Addigy global variables. Right? So we can build a single script and then feed in different variables for account name, account type, is it hidden or not, previous passwords, current passwords. We can load all this stuff into a single script, deploy it out to multiple organizations with completely unique values, and then be able to rotate it nondestructively. And that’s because we’re able to provide not only the the current credential that we wanna make sure is enforced, but also a previous credential so that if the service account does successfully have volume ownership, if if it has a secure token, that that’s not lost while we can rotate that password pretty much on demand at any time as needed. And being able to not only do that for our managed service account, but also leverage that account for semi automated healing of secure tokens for our clients. And so we have automation in place that says, hey. The scripting account is present. It’s got a token. That’s great. The current user doesn’t have a token or vice versa. Right? If one has and the other doesn’t, this automation kicks in to walk the user through, hey. We need your password so that we can fix your secure token status. And it just makes sure that both the institution retains decryption permission as well as the end user so we don’t end up in a situation where someone is is locked out of their machine. And so we we try to do this on on both fronts to minimize the amount of times that our technicians need to, you know, pull out that file vault recovery key. Right? And then work with these are getting into recovery mode. We’re we’re just doing everything we can so that we don’t lose time on the service desk for wiping machines and then restoring data from institutional backups or just straight up losing information if if the company’s not opted into, you know if they didn’t place value in that or someone was working out of their some folder that wasn’t backed up with OneDrive, so on so on and so forth. We we try to take care of that stuff in an automated and and branded and user visible way to avoid the ticket before it occurs, keep people happy, keep the service desk happy, and focused on other things. The goal with that is, like, you you wanna provide right? That’s that’s the business balance. It’s you wanna provide the best service that you possibly can. There turns into this conversation of, hey. We’ve we’ve spent hours and hours and and months and sometimes years building up some of these these script, these code bases. What are you giving away as part of the product? What are you giving away for free? But you always need to on the side of taking care of your team so that your engineers, your service desk techs are not burning out or being put into awkward positions they don’t necessarily have to be. And that also, of course, is is a benefit to the end users and the organizations themselves. Nice. There’s nothing more annoying to have that FileVault key not destroyed, and then users reboot to the machine. It’s asking for the FileVault key, there’s nothing you can do, and you’ve lost data. Yep. It happens. It does happen. Wow. And I know that the the sort of, like, savings there isn’t necessarily always quantifiable, but do you have a sense of, like, how much time this might have saved or, like, escalations that you knew didn’t happen because of this? Oh, jeez. We we have well, we haven’t tracked the the metrics specifically, even though that would be a delightful time. It’s every ticket where we have to deal with, like, a a as an explicit secure token problem, it’s probably a handful of back and forths or phone calls. We’re we’re looking at a minimum of of probably an hour of of billable or non billable time depending on the client contract. And across, you know, two hundred, three hundred, four hundred organizations, yeah, we we think that’s the investment is well worth it. There we go. Nice. Even just for The way I yeah. Sorry. Yeah. No. I was gonna say even just for your peace of mind, I can imagine just taking that off. But yeah. Simon, for it. Yeah. The way I look at, you know, what time savings has it made, it’s hard to put a number on because it depends on the skill of the service technician that’s calling the end user, the skill of the person on the other end of the phone, the user. You know, you can have a remote session with the user. You say, I need to install some software. It’ll take two minutes. It could take you twenty minutes to get some go into system settings to go and allow screen recording access. And if it’s a person who’s working a service desk and they haven’t got a Mac in front of them, and they can’t see what buttons they click, they’re just following a guide, and the poor user on either end is confused. Yeah. You’ve then got a situation where it’s really hard, and it takes a lot of time, but you then you might get someone who knows a Mac very well. You’re calling, oh yes, I’ll go system settings and allow that setting and you you’ve done it in two minutes. So it’s really hard to put numbers on sometimes on automations of how many hours has it saved. It’s really, well, we have run it hundred times in the last month, and yes, it’s run. That’s that’s a hundred less touch points we’ve had with our service desk. That’s how I see it personally. Yeah. No. Nice. And is there a a particular automation that you use at Air IT group that kinda that falls into something you would you would bring to the group here? Yeah. I think I’ll step it back a little bit. One of the main automations we’ve got is we have a lot of customers, and they have different device management platforms, not necessarily Addigy as the MDM platform as you call it or DMS as we call it these days. Getting the agent on the machines is so important because we need to get that device into our management platform so we can support it. We can get information from the device and know its state. We know what’s installed on device. What settings have been enabled? Hey. Has firewall been enabled? Yes or no? And then we could have that conversation with the customer saying, look, we need to go and get a phone the fault enabled on your DMS and get that key is screwed. And then, yeah, we just need to give that tool to our engineers as well. So there’s one tool that can go to need to deploy a piece of software, which I think is once it’s on there, it’s probably our biggest time saving. There’s nothing like a service desk engineer saying, I’ve got to go install a DDR product on twenty Macs. I’ve got to call each end user again. I have to get remote access. We’re going through that process. So it might get us quick on the machine, so on slow. Then we’ve got to install the software and give it all the correct permissions it needs to run. So for this access, allowing the security extension to run and things like that. You probably know sometimes what some of these may get missed. So it’s about consistency as well. So when you have it all managed in a management platform, we got the consistency. And usually, we can do it silently without even bothering the end user. And that’s where we need to be in a state of saying, okay. We’ve got the EDR in the machine, but then we need to say, hang on. Is that EDR actually working? Have the permissions been given? Can we get information, draw custom facts from them saying, oh, they didn’t enable a system extension on this device? And that’s where I see the automation going is just the whole life cycle of that experience. And at the end of the day, we can do it without bothering the end user if we do it properly. Wow. Yes. Oh, where I see it as the biggest time saving. Get the agent on the machine. Awesome. No. And this is a and I I love the the subtle Addigy plug. Thank you for that. But what we’re I sort of skipped ahead to this slide because I know just in our conversations when we were initially sort of talking about this session, In terms of what stops the most tickets before they occur, we, you know, we kinda covered these. I know Ross, you had talked about this first bullet point here, temporary admin promotion. I’m I’m making sure we covered that and, yeah, application deployment. You’re right. I think the pre built apps feature, I remember Simon us talking through this. But anything else you’d add here just knowing this is, you know, kind of some of the bigger ones that we wanna make sure people have their boxes checked on? The one thing that I would probably toss in there because, yeah, we the example I gave previously was primarily about, yeah, the secure token management and also client specific scripting administrator accounts. Temporary admin promotion also, depending on the organization, you know, can be a big one as well. And what feels like a long time ago because time is a construct, I put together a script that was fairly resilient to try to break it in a lot of ways and ended up with something I’m pretty happy with that allowed our users to go into, MacManage, go into Addigy self-service, click a button, and it just says, you apparently need administrative rights on your computer. That’s great. We’re so happy for you. Tell us why. They type out a little message into a note of script pop up, and then boom, that creates a service desk ticket. The user gets temporarily promoted to administrator for up to ten minutes, and then it rolls everything back and buttons it all back up. And then our service desk can, review that ticket just to make sure that they wrote something intelligible. So, like, I’m updating Slack instead of, you know, Tim Cook reached out to me and wants to see what’s on my screen. It it just turned into a great way for organizations with that with that acceptable risk tolerance, right, of we’re allowing our users you know, we don’t want everyone to be an admin all the time. Okay. That’s fine. We can write a script for that, make sure everyone’s a standard account. That’s great. But they have updated their end user license agreements. Right? That’s a you as an employee of our organization, you acknowledge that you are fully financially and legally responsible for what you do to your work computer while you are while you have administrative privileges. Everyone signs off on that. Okay. That just allows us to say, organization is given permission for that. That eliminates all the tickets on our side and for, the organization’s internal IT or as needed. And all we have to do is make sure, yep. That looks fine. That looks fine. And if it doesn’t, the ticket’s already in our system. So we can just respond to user, hey. We saw you put this through, you know, yesterday morning. Just checking in. Can you give us some more details? Again, this is just for forensic purposes. We always wanna make sure the clients knows. We respect your privacy. We want you to do what you gotta do in your work machine. When it comes to admin privileges, though, we just need to make sure that if something comes up in the future, we’ve got a paper trail and say, oh, when you try to install this print driver, something went sideways. Let’s take a look at that print driver, things like that. Awesome. Very cool. And, Simon, yeah, I I didn’t know if you wanted to jump in here about prebuilt apps and just application deployment, anything else that you you kinda maybe didn’t cover before. But Prebuilt apps. Absolutely brilliant. What I always say to our service team is go with most lowest complexity way of deploying software we have. If it’s in the catalog, use the catalog. I have to thank Addigy again because the catalog they’ve got is absolutely fantastic and is growing. It’s saving us so much time and we can point to service engineer saying, yes, go into go live deploy. There’s a software for the end user. You’re not remoting onto the machine and having to download the software and making sure you get from the right source and yeah, causing making something really difficult that’s really easy to do. And then the second thing is yeah, we can do custom software. If the customer needs something very specific, if we’ve got some condition check needs to be done or there’s some other supporting file that needs to go along it. It could be a license key that very specific to that software and it has to be deployed in a certain way. Yeah. We can get our internal Apple department as we have to go and create that scripts, and we’ll go through the few minutes about testing and what process we go through. But, yeah, then deploy it that way. Very cool. Thank you for that. And we’ll move into actually because I know we had talked about this sort of automations that we’re, you know, you’re implementing, but this was actually a great list that Ross, you had put together initially, and I know Simon, you probably have a few of your own too that you’d recommend. In terms of the the tools that are helpful for you, I’ll leave this up here on the screen, and and maybe there’s some that you wanna dive into a little bit more deeply or some that you think are are just worth that extra, you know, like, need this now. What yeah. I’ll let you take it away here. Sure. Yeah. There’s as users in your in the audience right now, you can probably tell that I’m a huge fan of open source just by looking at this. A lot of great tools here. There’s no need to reinvent the wheel. The Mac admins community is is large and very, very talented. And a lot of times where there’s an open need, someone’s gonna step up, get something built in GitHub, and the community starts adopting it. Some of the tools, I’ll just shout out real quick. Huge, huge respect and appreciation for a suspicious package. It’s been wonderful, wonderful open source tool that allows you to just examine a package or an MPKG and see everything that’s inside of it. Right? So preinstall, postinstall scripts. You can take a look at what files are being placed where in on on the device when it’s being run. For MPKGs, you can actually delve into every subsequent package being nested inside of that. And so you can really, really dig in and and get a great idea of what what’s happening on a specific system when it’s being run. Ads ended up being really valuable for us not just to create condition scripts. Right? So we know that, oh, if if this, you know, p list file is present on the machine, probably means this package was run at some point. Otherwise, where would it come from? And can also be helpful if you get a package that you know it needs to deploy, but you’re seeing some really unusual behavior from it. Give you an idea of what are the post install scripts, why does it keep throwing an error. Oh, that looks a little off or maybe just might not play ball with some of the EDR tools in our environment. It just gives you tremendous amount of visibility. Right? So you can you can adapt and modify to things that are happening on the system. Yeah. I can give you a good story suspicious package. We had a customer with some software they wanted installing, and they’ve already got it on the Macs already. So they wanted a new version. So I run it through a suspicious package, and it was some tracking software. They said, oh, we use this software that if we lose a device, we can go to the console and we can track where the MAC is. So if it’s been stolen, we know where it is. Well, it’s it’s we didn’t go to do things off of you reboot the machine. If Firefox turned on, good luck. But I looked at that, and I I went suspicious package, and you can you can check is it signed and stapled all the scripts, which is fantastic, which is what you should always be doing first, make sure it is signed with Apple. But then I looked at the entitlements, and I went, this software is a bit strange. They asked for the camera and full disk access and the microphones. I thought it’s for tracking. And I tested in the virtual machine. And as soon as you install it, it goes, I want camera permissions. I want microphone permissions. I want access location permissions. I want full disk access and accessibility. You go, that’s a lot of things that software is asking for. And what I found out, I I was looking at my laptop. I was testing going, the camera’s just turned on. Oh. And then I asked. Scary. And then it was really scary. And I looked to the and I came back to it later, and I logged back in. The camera, the light went on, and then off. Okay. We are. I had to have a conversation with a customer, and I got into the admin console. And I found out what it was doing, It was taking photos of every so often, it would take your photo. And every time we logged on, it would take your photo. Instantly, I I said to the customer, this is what it’s doing. And I went, we didn’t know it does that. Got rid of it. And that suspicious package, and, yeah, it just revealed more that the customer didn’t realize what the product was actually doing. So, yes. It, yeah, it has saved some of our customers from those situations where, yeah, if someone in the company noticed they’re using that, they might go, hang on a second. Yes. It went off very quickly Oh. Of every single Mac. Yes. Oh, man. Well, I trust Ponce and our IT team here at Addigy, but I would otherwise be like, hey. Can you guys, like, look at this? So, yes, suspicious package recommended just every time you download a PKG. Open it and inspect it, not just for the automations, but for some security in general. Wow. So Oh my god. And, yeah, if and if you’re coming at this from the other side of things, if you’re not assessing an incoming package, you can check out the package. Packages, I’m just gonna keep saying this word until it loses all meaning, to build your own PKG files. And then real fun, it hits the same architecture you’re familiar with. So you can choose files that you wanna populate in different places. You can choose whether you want those files to be at root level or at the current user level, and pre and post install scripts as well. And so oftentimes, if you need to send something off board, one of my favorite things to do with, with packages is to create uninstallers or off boarding, packages so that we can say, you know, a client parts ways with us. Two months later, someone’s like, something’s stuck on here that we didn’t expect. Right. Here you go. Run this package. It just looks for a couple common things, cleans them out, calls it a day. Or if you just have your own installers and you’d rather not, you know, echo, touch, or cat files in plain text through your scripting. Just choose where you want it to land, dump it in a package, get it out the door. And then all of these are about visibility and managing MDM, DMS, DDM. PPPC utility by Jamf, spectacular tool. Amazing profile editor, another very, very powerful tool. If you are curious about new mobile config files, new domains that are being managed through MDM profiles, being able to spin these types up very, very quickly with transparency and then links to documentation. Absolutely indispensable. Nice. Very cool. And where can folks learn more about this? Because I know pseudo aid, this is coming from I’m I’m assuming actually, you actually probably have an article that talks about this or or many different sort of pieces that sort of piece together. Hey. Like, how can we solve this kind of problem? Yeah. A lot of this stuff is if if you’re watching and you’re not in the Mac admin Slack, get in the Mac admin Slack. What are you doing? So come join us in there. We’re all hanging around and and love collaborating together. There’s a great sense in our community about the rising tide. Right? And so it’s what anything that works for one of us is gonna work for a lot of us. And we just want everyone’s lives to be easier. So links to all of these can be found in and about the community. I do have a couple articles, especially on Nudge and Utility. On PseudoAid, I’ve done presentations with the Mac Admin’s conference out of Penn State and a couple weeks ago at with University of Utah. It’s one of their libraries about utility, which is used for to get and set default applications for different file extensions and type identifiers. I’m gonna ask some information there. If anything catches your eye though, these are all except maybe for packages itself, have very hard to mistake names. You might have to disambiguate a little bit with enough named packages to make sure you’re at the right place. But, yeah, find us in the community, and, a lot of things can just be googled and leveraged to to great success. Awesome. Yeah. I would encourage folks to to check all those tools out and to go to Pseudo Aid if you have more questions there. And obviously, yes, get into the Mac admin Slack channel, please. Please. But switching gears a little bit more here to the compliance side of the house. Simon, this was an area you and I talked a lot about in terms of just where automation can really help out on this side, and especially with the, you know, coming out of Cyber Essentials in the UK. If you wanted to speak a little bit to that. Well, first, even just tell us, you know, what what is Cyber Essentials and and sort of how how automations kind of filter into to help or what kind of automations you now need to have in order for for that to be compliant. Yeah. So the compliancy thank you. The compliancy with Addigy comes in in in two sections. One, there is the device and how it’s managed, and we need to set certain configurations in the device. So it could be is a device encrypted, the hard drive, so turning file vault on and destroy the key. Have we got firewalls turned up? Is a screen locking applied? Now the great thing is we can all do those through MDM or DDM configurations. Absolutely brilliant. But the other things we need to look at is another part of Cyber Essentials is for the compliance. The software, if it’s found to be vulnerable, has to be patched. Now the spec for Cyber Essentials is if a piece of software and operating system has a security vulnerability with a CVS rating of three point one of seven point zero or above, and the vendors release the patch for that piece of software, we have to get it passed within fourteen days. So it’s a big undertaking to make sure we get all these software and all the operating systems up to date. So we can remediate against that. Prebuilt packages, fantastic. You can set a deadline of fourteen days. It will go ahead. It will patch that software. If there’s not a software that’s not in that catalog, we can patch it. And then the operating system, we can patch it with declarative device management and get that enforced within fourteen days. And that has always been a major hurdle. If you don’t have the correct tools in place, it’s it’s hard. Really, really hard. Addigy has just made keeping compliance for our customers just really simple. Most of the time, they they’re not even bothered. The end user doesn’t know we’ve remediated some software. Yes. They get a bit squeaky about when we have to force reboot because I haven’t rebooted the machine after fourteen days after the update is gone, and they got one hour deadline to reboot the Mac. But they learn to live with it. It’s just fantastic. So, with Cyber Essentials, when it comes to the automation, we’ve got that. But also, we need to prove that device is compliant. So we can create the custom facts that will go and look, is that screen locked in place? Is a FileVault turned on? Because with Cyber Essentials Plus, there’s two sides of Cyber Essentials, and you can go for the more stringent option, which is the plus version, which is audited. So we got to turn around to the auditor and say, there’s our customer’s fleet, and this is a state they’re in. And all the software that is vulnerable is not running on the machines. This is what they’ve got. And they can turn around and go, yes. Thank you very much. And they got all the information to hand. So we need to not just create the software packages and deploy the software updates for the operating system. We also need to create the custom facts to go and just validate for Cyber Essentials that they are compliant and remain compliant. Because one of the new changes this issue, Cyber Essentials last year last year used to be snapshot of when you were audited that week when it was done, and then you come another year and your software’s fallen out of compliance. Your machines have been updated because those customers asked for it to turn off, but now we’ve got to continuously prove that we’re maintaining compliance. And Addigy’s got all the logging in there when software was deployed, so we could say, yes, that was deployed two months ago and was remediated in all these machines and all the software’s up to date. And that is really, really important to our customers because we try to push all of our customers. Well, not generally push, but just say to them, look, you need to be Cyber Essentials compliant because you can’t work with a a government body or a public company without being compliant in the UK now. If you wanna get a government contract, you can’t do anything. If you want to work with a large organization, the first thing they’re gonna ask is, are you Cyber Essentials compliant? And if you don’t get it, you don’t get the contract. Simple as. And then we can’t let other companies go, yes. They’re Compliant, and they’ve remained compliant. So, yeah, it removes a lot of that friction, lot of the questions later on when we get that horrible questionnaire from a new potential client, what a customer’s got, and it’s it’s like, oh, no. No. No. We’re fine. I can prove it. Oh, wow. Okay. Well, thank you for that. That’s I mean, I think, really, for a lot of folks here, you know, maybe if you’re in the UK, making sure you have that in place. And just knowing it is it is enabled in Addigy, a little bit of the automation piece there. So very cool. Thank you. And alright. So the scalability issue here. I shouldn’t say issue because it’s not an issue because you guys have this handled. Right? This is you know, how do you how do you test a script before it ships out to forty clients and forty clients? Nothing. What about, like, three hundred? So walk us through sort of like that process for yourself. I know folks here on the call might have some, you know, best practices, but what are some of the the kind of like walk us through the, you know, kind of your your details that need to be sort of checked off here. And I don’t know. Simon, if you wanna start, and we’ll we’ll switch it up because Ross has been kicking us off, or or which one? Yeah. Yeah. Sure. I’d love to. I think I think the the first thing we have to start with is you need to get your information together. You’ve got to do a static review of what you’ve got out there because, yeah, you could run a script or an automation to a device. It could be an EDR product, for example, you want to get deployed. You gotta do a static review. The customer may already have an EDR products installed on their on their devices, and you don’t know about it. And as soon as you install it, they’re gonna conflict. And it won’t be a machine is running slow. It I’ve seen somewhere people can’t log into the device. It it it it can be that they that much of a problem. So you need to go and review your fleet. Get the Addigy agent on there. Get those facts. Get the custom facts. Look at what software is installed. What’s ringing on the device? Because, yeah, you don’t wanna up that situation where you think, I’ve got to deploy your software, and then it’s caused a huge problem. You also need to think about, again, what’s your intended state afterwards, and what assumptions need to be made. And I think the next polling question is what privileges the software require? It’s great pushing out the EDR product, but again, you’re gonna have to configure that piece of software to automate it. So it’s got all the relevant permissions. Has it got access? Has it got accessibility? Can it have all of those? And can we automate it so it doesn’t prompt the user to enable those settings because we interpret the dependencies that are installed in that software. So, yes, suspicious package. Fantastic. Check it. See what dependencies it’s got. You’re quite amazed. And also, look what could stop the deployment. Again, it could be they’ve got some existing software that will conflict. I was thinking of some software where we get conf conflicting problems. There’s there’s a certain creative cloud product from a certain company called Adobe, which every year they go and release a brand new version of their suite. And you have to make sure in the company that everybody’s using the same version of that software. If you’ve got twenty people in the studio, and one person, I want to go and start using version twenty twenty six of this software, and I’ve gone and edited this file, this InDesign file, and then I’ve handed it back to people in the studio to go and continue their work, and they open it and goes, oh, sorry. You can’t open that file. You’ve got to make sure you’ve got people locked down. They’re not gonna go updating their devices to newer versions of software, so you’ve got to automate the install. Thank goodness Adobe actually have a way of disabling the self-service store. But then you’ve got other dependents you need to think about. So a lot of customers will have font management software and have a a plugin. It will work with last year’s version, but this year’s version, it it might either not be compatible or not installed for that version. So again, you’ve got dependency there and we’ve got another dependency that might have their own custom plugins that have been developed and they don’t work in the new version. So you need to rigorously test, which I’ll go through all. I think, Ross, you’ll go through a bit of your testing process of how you rigorously test software be before you deploy it. But, yeah, you’ve you’ve you’ve really don’t wanna be in that situation where you’ve got that one that’s deployed a new version of Creative Cloud. I’ll give them the anecdote. Someone decided to install a new version of Photoshop, and it’s linked with an InDesign file that the studio used. So they’re editing in Photoshop, open InDesign, and it crashes straight away. And you you remove InDesign. You clear its preferences. You think you’ve totally sanitized the machine. And you go and open the file, It crashes straight away. It loads up, then push closes. And you go, oh, let’s let’s go back to an InDesign file from two weeks ago because we know that was working. Oh, it crashes. And you can’t answer why. It’s because someone’s got an edited Photoshop file that’s linked in with it, which you didn’t know about in a newer version, and it’s just it causes chaos. So change management, especially with Creative Cloud. Good hint. Make sure everyone’s locked on the same version, and then you automate that change to get everybody on the new version, which I’m sure Russ will go into the moment his his strategy for deploying software and how he tests and checks everything is working, which I’ll hand it over to you, Ross, if you want to cover that. Yeah. Of course. Sorry. You just it’s you just lit up some candles in the back of my head from a long time ago. I was like, oh, no. Yes. I’ve been there. But, Simon, to a lot of your point, this this makes a lot of sense. And and oftentimes, the the first step in scripting is, is this even worth doing? Like, what are what are we actually putting together? It’s that moment of, okay. So we’re building this for a single organization. That’s great. We’ve never heard of this application before. That’s fine. They have one computer. This is getting weird. But the benefit of it is that you you need to be scalable. And if you’re doing the research right now, white label the heck out of it. You know? It’s it’s never gonna be fresher than it is just at this moment because I, for example, could not tell you much about the monotype plugins for a creative cloud right now. But when I was first dealing with that a couple years ago, I was fairly adept. And so if if you’re gonna put it together, if institutionally makes sense for you to put it together, treat it as something that’s going to be part of your workflow for years to come. Right? So build it not just for this one organization. Keep your variable names generic if you’re inserting specific registration tokens or keys. Get those in as global variables so you can assign it to different company policies in the future. Right? Just build it so that you can build it once, document it once, and then come back to it as often as Once you know that, okay. It’s it’s worth doing. We’re gonna put this together once we think it works. Then the testing phase turns into just a lot of work, and you can’t zone out no matter how much you’d like to. Because you’re gonna be testing at we always start off first in virtual machines. We always recommend, of course, to stick with Apple’s OS support cadence. So you’re doing n minus two, current OS and the last two before it, anything else still gets security updates. Because hopefully, hopefully, hopefully, your client base has committed or accepted your gentle prodding to only run secure operating systems. Right? Because you wanna make sure if if you have a Mac in production that is on a Mac that it’s on an OS that’s no longer getting security updates, that’s a huge problem. Right? And for a lot of industries, for a lot of organizations, they’re gonna kinda blow that off. But as a service provider, it’s really a big deal because that’s a threat factor that we just would prefer not to deal with. But know your fleet. If you have to manage older OSs, test against those two. So I’ve got, you know, five or six VMs that I will just throw spaghetti against to make sure that nothing crazy happens, or if it does, to at least document it. Because a lot of times, it’s not that, you know, this particular code that we wrote is incompatible with Mac OS thirteen. It just works differently, and that’s okay. As as long as you know about it, as long as you communicate that to your clients and to your service desk, that’s totally fine. And so we start with virtual machines first, identify any major OS related issues, then move on to production devices. We’ve got a couple test MacBook Airs, a test mini that, again, throw all the spaghetti against because they’re not daily drivers for folks. Once we’ve made sure that we don’t see any unusual behavior in that hardware, if we’re starting with a small ring, if this is really for a certain number of organizations, we’ll check our internal documentation. And to Simon’s point, what are the EDR agents that are on the machine? What are the things that we expect to, interface with other parts of the Mac that this application or the script is going to interfere with or attempt to coexist with. We’ll call it that. So we set up those environments on those production devices as best as we can, run it. Okay. We think we’re good. Great. Then it turns into if it’s with a single organization is often some of these quests originate from. We recommend touching base their primary context. We’re looking for volunteers, and these will be folks who are not hammered down with a really strict deadline right now, folks that have worked with us in the past or just tech savvy or tech forward. One of the best groups that we can find for that are users of organizations who beta test operating systems. You know? Because if you’ve got someone who is confident enough with their relationship with their computer and with the tech stack at their organization. Be like, yes. Of course. I wanna play with with, you know, Mac OS Golden Gate, you know, and make sure everything works. And if if they’re that level of savvy and communicative, those are the perfect users to begin running these these automations against and and getting feedback on. From there, then you just slowly increase the scope. It’s possible through the use of flex policies to target, you know, specific groups of devices at an organization or across multiple organizations if you’re building something that’s that’s much grander in scale. But it’s just about always just increasing the ring that you’re applying the script to in in measurable jumps and ideally with enough organizational consent and transparency so that if something doesn’t look quite right or if something goes sideways, you hear about it sooner rather than later. Right? And so that every time you expand to the ring, there’s at least that little bit of breath so that folks can get back to you. Hey. This I I don’t know why, but something’s kinda weird with Outlook right now. Can you check it out for me? Maybe there’s some correlation we didn’t see before. And so yeah. But you just you just keep keep increasing that scope until you hit your intended target. And ideally, because you white label the code as you put it together, you can just make a little guide for other engineers or administrators in your organization that say, hey. We put this together. It’s only going out to fifty machines today. But if someone runs into this in the future, do this, do this, do this. It’s already built. It’s ready and waiting for you. Awesome. Well, Ross, Simon, thank you for that. I know that’s probably the the scariest part of of the process. Right? So it’s it’s good that we actually, I do wanna jump ahead a little bit to the this question really. And again, I mean, has been a running theme throughout the entire day about AI and automation, agentic, Apple device management. But what I really wanna caution folks against is is some of the stories that I’ve heard from you both, which is, you know, like, where where can AI go wrong? Like, what what should we be watching out for maybe in some of your testing? You know, like, just understanding where to use AI and where? Maybe add a little bit of caution there. And I’ll hand it over to you, Simon, because I know you had a you had a lot of thoughts about this when we we first brought this up. Yeah. I think myself and Ross, before this meeting call, we’re having a a conversation about documentation, because we take a totally separate approach to our documentation. Ross used to be a copywriter, if I’m correct. So you’ve been there, done that, and you know how to write documentation. For myself? No. I don’t. So where have I find AI to be stupidly useful is in documentation. So you you feed it all your scripts. You tell it you set an agent to create all your documentation in a certain format explaining what the script is. And, yeah, you hope he’s he’s got the right results of saying what the script does, and he’s not gonna edit your script. But, yes, when it comes to scripting, you have to be careful because these AI agents, as you want to call them, it could be an LLM, it’s only learned what’s out there on the web. And it may be rubbish. It may be a script from ten years ago. Same with humans. Someone will go to Stack Overflow and find a script that’s ten years old and run it on a Mac. You come on. You need a robust change management process. So with AI, be very careful of what output comes out of it because you, you know, you don’t wanna deploy a script that’s going to go and break a device. You’ve got to manually review that script. You’ve still got to have that skills of how to read Bash. You need that rigorous change management process in place where it’s gone, it’s been peer reviewed by somebody else before you’ve deployed it, and you’ve tested it, and you’ve tested it. So that will be yes. Take with a pinch of salt the output you get. However, AI can be useful as a good starting point. If you came to me twenty years ago in a student university and asked me to write a bash script, I probably could have written a loop for you or something like that or an if statement. Now I can’t remember how to construct it, but I can prompt an LLM to say, I want to do an if statement with this. This is what I want to find out. You’ve got to give it the context to go and get you want and confidently rather than being wrong, it should be right. But you still need to validate. Yes. The context is everything. If you just say, go and create me something, it might not know the nuances that it needs. Yeah. One of the biggest risks that I’m finding at the moment is we’ve got LLMs. You’re asking a question. It comes back with an answer. You think about it. You process it, and you action it. What we’re now seeing is AI agents, whether or Tom is to do certain tasks. I’ll give an example OpenClaw, which is released. And we’ve got Copilot Cowork, which Microsoft released to compete against it. And they can be very, very scary because they can go out and they can do something on your behalf. And it’s doing something that you’re not aware what it’s doing. It’s not authorized to do. And it’s just gone undone it. I’ll give you an example what it could do. You say, I’m having this problem. I need help. Get me help. Or you find out it’s gonna go in and say, okay. I’m gonna create create an email automatically, and I’m gonna email some people. I’m gonna write what help I need and go, I need help with an API. I’m having an API problem. Well, that agent’s got access to all your data, and it could go and go, I’ve got this problem. Oh, here’s my API key that you’ve got stored in the text file. I will put that in email. Then I’ll go in email. So internally, but then I’ll go in an email some support Addigy. Fantastic. That’s a good place. But just to be double sure, I’m gonna also email Jason at the same time and include him in the email. And they will go and just do this, and it’s really quite scary. I’ve had a true story from somebody where they said, we turn this on, the ultimate ultimate and he told it to just reorganize my week, my my calendar. Just can you go and reorganize it for me? And what it did, it canceled down every single meeting they had that week. We organized the calendar. So it was nice. All the meetings were in a in a better, you know, time slot. But then he went, oh, we’ve got a meeting about this subject and this internal meeting, but I know this customer had this problem. We will also invite external customer to this internal meeting. And it sent the invites out automatically. It did it autonomously without anybody asking. And this is where it could get very scary with AI. You have to make sure you got those guardrails in place that one is not getting that data and exfiltrating it. I I’m gonna give a perfect example. I I got a Copilot license here at Air IT, and the first things I thought I’d go is I’m gonna ask, can you search my OneDrive? Have I got anything like a password or an API key stored in the file somewhere? And it came back with about ten results. And I thought, oh, I’m pretty clean. Problem is if I got breached in any way, someone could very easily assassinate agent. Oh, can you give me any credentials? And it could get out. So I’m very quick to delete them, told the bot to retrain. So you’ve got to be very careful because, yeah, it can get that API key, like I said earlier, and then send it in an email, and you don’t know about it. It may be a script, and you’ve got an automatic remediation. You think this AI will remediate it for you. You don’t know what it’s doing. It could be getting that script from ten years ago and redeploying it, and it breaks the machine, because it doesn’t know any better. You still need that human touch. And I think where AI goes wrong, that’s where it can go wrong at the moment, and it’s vastly changing. Yeah. Open Claw changed it yet again because everyone’s going, well, that sort of automation is no red flag. We don’t do that. You know, Google Gemini said, we’re not doing that. As soon as OpenClaw came out, they’re like, oh, next week. Oh, we’ve released it. So it’s very changing. It’s changing a lot at the moment. So, yeah, be very, very careful. Make sure the data it’s got access to is well guarded, and that’s my recommendation. Oh, well, I’m happy for our our IT horror stories. Oh. Article later. But, no, I mean, the governance piece is so huge, and I I I appreciate you kinda, like, like, you know, putting a finer point on that because that at least at Addigy, we knew that before we did any work with AI features, we made governance really an important layer of that even just the does a human always get to approve this? What can actually the agent even do? Are we wiping out any of those potentially catastrophic things? And and you’re right. I mean, like, you know, all this talk about AI, like, at the end of the day, you will still need a human being with the expertise to be able to, you know, check things off. And that’s that’s really where I see, Ross, you had mentioned, you know, in terms of, you know, where you’re leveraging AI or what you do to train AI. I mean, you you really have like an interesting take here where we’re sort of, you know, kind of like shifting into the documentation side of things. If you wanna kinda dive in there and sort of how you’re how you’re thinking about things there, or if there’s anything you wanted to comment on what what Simon just mentioned, I’ll sort of I’ll move us on to this next slide. Yeah. Yeah. Yeah. Yeah. Yeah. Just coming at it from from both directions. One of the things that has sort of become evident, and this is very much to Simon’s point of, like, you you it’s great to use the tool, but there needs to be expertise behind the people observing and using the tool. Because otherwise, you won’t know what questions to ask. You won’t know what to even look for. And in a way, that’s sort of made all of us who are using and leveraging AI tools into managers just without the HR. And so it’s anytime you’re interacting with an agent for something that’s coding related or looking amass with some resources, looking at, you know, scripting solutions, all that’s great. And it it involves what can sometimes feel like a different skill set, what we’re used to doing. It’s it’s one thing if I can sit here and, you know, chug out a five hundred line script if I need to. It’s another thing if I’m managing a small team of very dedicated interns who very much want to, you know, get head pats and told they’re doing wonderful work. You have to tell them exactly what you want them to do, and you have to be so, so specific. And and it it just feels so different than to your point earlier. It’s like, I’m going in Stack Overflow, and I’m gonna learn what I need to learn about Mac OS Panther. It’s gonna be great. And so dovetailing into sort of the work that I’ve been leveraging AI for within Antiva. Antiva is a very AI forward company. And one of the biggest opportunities as the person who manages our customer facing knowledge base. Right? So we’ve got support dot antiva dot com, which is our Apple knowledge base. We have a couple platform agnostic articles on there. But anytime to my earlier point about, like, automating people or taking care of things before they become issues. It’s not always just, oh, a script needs to run to do this. It’s it’s education and outreach. It’s letting you know, hey. You might see this pop up that says, I need your password. You should be worried about that. Here’s the notification that are coming from Antiva. You’re the ones that are, you know, part of making sure that your technology is secure and is in good shape. And that can also be how to turn on OneDrive syncing. To to Simon’s point about how important it is getting agents installed, we’ve got an article about how to install the Addigy agent and MDM profile. Right. And so because of this documentation that I build both internally and externally, one of the things that we’re we’re working on is ensuring that our internal agents have the best knowledge possible. And so when I’m creating new documents, when I’m updating documents for our internal use, it’s always this question of, you know, be as unambiguous as possible with language, you know, be consistent with how we refer refer to things, and then take articles when they are updated and polished and ready to go and get them into that organizational context. And so a lot of the documentation, strategies that I go through are about, maintenance. So that it’s one thing if an AI agent goes out and pulls something from the Internet that is kinda right, but not really relevant anymore for today’s technology. I I’m deeply concerned with making sure that our internal agents, when they look through our institutional context, are getting the best information about our Apple support offerings, about the tools we use, and how we support our clients so that someone in another department who’s never spoken to me before can still ask, how do we deploy Huntress? I don’t know. Alright. Well, if here’s an article that’s put together that’s got a last modification date of a couple weeks ago, that’s probably up to date. And so we can have that out there, for folks to access. And so in the same way, that’s it’s very important for knowledge based articles, both external, internal, to remain updated so that people looking into them just by browsing are getting the best information, getting accurate information. It becomes so much more important than it has in the it’s always been important in the past, but it feels more relevant today, because of the possibility of AI agents ingesting that information that could be out of date and then causing problems for you and your clients in the future. Our script library specifically, what a wonderful slide, is is in a similar spot, right, where because when I first learned coding and scripting in Objective C, people were very strict with me about how much commenting I did because when this compiles at runtime, you can’t have things take too long. Nowadays, Macs are are almost absurdly capable on a hardware standpoint. And so comment your code comment your code thoroughly and constantly. It is okay if that one kilobyte script is now a five kilobyte script because you included clear definitions and explanations about what it does, how it does it, resources you used so that when you’re looking at that script in the future, not only can you read it like a narrative, you should be able to read it like a book even if you don’t understand the commands because the inline code describes, hey. We’re looking for, you know, users who have a UID of over five zero one here. Okay. Even if I can’t read that bash line, I know what it’s doing. And then we do this, then we do this, and then we do this. It’s my hope with documentation that you never have to Google something twice. And that’s why if you’ve got your code, if you got it from a colleague on the Mac admin Slack, if they linked you to this incredible resource first party, like, from the developer themselves, include all those links as well. So you’ve got this incredible springboard and this backlog of information that you’ve learned in the moment as you’re putting this together and make sure it’s all there for future use. As long as you have that kind of care being set towards the scripts you’re putting together and the documentation you’re building either in line inside of your bash and z shell scripts or if if you’re using, you know, Kaseya’s IT glue or or other internal documentation sources. As long as it’s up to date, you’ve got your, you know, your author information in there so that your colleagues can reach out to you if they have questions. You’ve got your time stamps in there so that folks know, oh, this is an incredibly guide. These screenshots look a little weird. I don’t think Mac OS looks like that anymore. They can see real quick, this was updated in twenty twenty one. We should probably double check that. Right? As long as you’ve got those foundations laid, then that gives your AI agents a healthy jumping off point, not only for how they’re going to work for you, but for how they’re going to ingest your information and then feed that back to other teams, other departments, and your clients. Yeah. Ross, thank you. That’s you gave us so much to think about here, and I I appreciate this because I know you’ve done entire sessions on documentation and just the importance of that. And really just to note for everyone here, and you know this. Right? The AI is only as good as the context you give it, which is coming from our human experts here. And this is my my subtle plug here for Addigy about our AI Script Assist. For customers here who haven’t tried it, I would encourage you to get into that. And I know, Simon, you actually had mentioned I think you you’re one of our customers here. So yeah. Tell us. Yeah. Go and enable it because it’s great for creating your scripts and editing your scripts and, yeah, refactoring if you need to. But it actually has a feature in there for actually explaining what the script does. So if you go into there and click the button, say explain what the script does, you can then I recommend copy pasting it. Go put it some documentation somewhere. Get someone to learn from it, because it actually does a really, really good job. Yeah. Just put that knowledge somewhere. At the end of the day, this AI, it’s it’s it’s not automating things people away from doing the things. It’s about getting that knowledge automated. Because, yeah, we’ve we’ve got we’ve got Mac admins in our company. We’ve got Apple department. There’s only limited of them, but we’ve got hundreds on the service desk, and this automation is really sharing all that knowledge and empowering all the others. So, yes. That’s my final remark and my little sound bite I wanted at the very end. Thank you, Angela, for, yeah, bringing me straight back in. Awesome. No. Thank you. And thank you, Simon. Thank you, Ross. I could keep talking about this. We’re out of time, so I will I’ll hand it off for Tober to do our wrap up here, but I’ll encourage folks here to connect with Simon and Ross on LinkedIn, and obviously too, jump into the Mac admin Slack channel where you’ll find all these resources and more. So thank you all. Have a good rest of your day.
Build Once, Deploy Everywhere
Scripting & Automation that Scales
The automations in this session stop tickets before they exist — secure token self-healing, temporary admin promotion, application deployment — shown by the people who run them in production.Speakers:
Speakers: Ross Matsuda, Systems Engineer, Ntiva, Inc. Simon Howes, Service Delivery Manager & Accredited Apple Technical Partner, Air IT
Additional Resources
- Zero Touch Deployment
- Open source PBA plug in
- Apple Business Overview
- Submitting an Apple Feedback via Feedback Assistant
- MDM Updates Commands Removed from OS 27
- How to Defer OS 27 for macOS, iOS, iPadOS, and tvOS Devices
- OS 27 Is Here: What Enterprise Apple Admins Need to Know Before They Upgrade
- SSO Tool

See Trusted AI in Apple MDM
Describe what your Macs need in plain language. Review what the platform proposes. Approve and execute in real time, not at the next check-in.

