Polish Up Your Best Practices: Perform OS Updates without Interrupting Operations

Kyle Bareis
April 21, 2020

Welcome to the second installment of our three-part blog series focused on tactical approaches to monitoring and remediations. In this piece, we’ll address how alerts management and a strong communications plan can help IT administrators prepare end users for a macOS or iOS update at any time of year.

For companies with strict regulatory or security requirements, rolling out a new macOS update can feel like a major coordinated event (whether or not it should). Wherever you stand on the question of preparations for updates, we recommend that your team examine the betas update inside and out, identify potential issues, and communicate clearly before and after the release.

Your ultimate goal is to provide Apple device users with the support they need for continuous operations, and updates ensure that this is possible and that your operations are secure. Take these four steps in preparation for the next macOS or iOS update to ensure operational continuity and security.

Step One: Identify Potential Issues Before They Occur

When betas for the newest macOS are released next summer, take advantage of these previews to truly get to know the new OS and identify potential issues within your environment.

For example, just last year, many businesses found themselves looking for extra support during their rollout of macOS Catalina. Because one of the improvements this upgrade includes is a shift away from supporting 32-bit apps, IT admins who support Apple devices found themselves facing a question: how many devices might this update potentially impact?

By asking this question ahead of time, you were able to proactively address any issues that might impact business continuity before they arose. You can also take advantage of Apple’s program specifically designed for betas called AppleSeed for IT. Any customer that has Apple Business Manager or Apple School Manager has access to prerelease software months ahead of when it ships.

Step Two: Use Device Facts to Identify Which Devices Will Need a Remediation

Let’s keep going with our 32-bit app example. In this case, IT admins with Addigy already have the visibility they need into all the managed Apple devices in their networks to identify which Apple devices will need their attention before moving to the new OS. They simply had to run a check on the device fact: Does this device contain applications that rely on 32-bit architecture?

While the 32-bit example illustrates a potential incompatibility between a new OS and an older model of application, there are other possible issues than may be more serious. By testing betas, you can also vet them for compatibility with your business’ regulatory and security requirements, which may be industry-mandated.

Step Three: Create Alerts or Design a Remediation

Once you have a clear view of which devices require attention, your team can create a plan of action. If the application incompatibility is mission-critical or could expose your company to some form of security risk, you may want to push an update or pull that application from all Apple devices enrolled in your mobile device management solution. However, we recommend using this direct remediation approach only when absolutely necessary.

If the issue is not critical, you may prefer a softer approach before (or after) the new OS has been released. Depending on the needs of your organization, you may want to give end users the option of updating at their own pace.

If you decide to go this route, it’s best to set up a monitoring item to help you keep a list of devices that have not yet updated and alert you to any changes in a critical device fact. This can prompt you to reach out to the user and request their action on a timeline that works for them.

To return to our 32-bit application example: Say a new device on your network that entered through your BYOD program has 32-bit applications installed and will need to update to the latest operating system. There are a couple of ways you might approach the message you might want to send the end user in question:

  1. We’re going to take preventative measures to upgrade your applications in preparation for the update. Here’s when you’ll see these changes!
  2. Please run this OS upgrade in order to continue to meet our company’s standards. Please note that some applications might not work anymore and others may need to be removed.

Either way, it’s important to include a communication plan as part of your remediation roadmap. Your end users need to know what steps are being taken, in part because their trust in you and your team will help everyone do their jobs well. Mobile device management solutions provide the IT department and end users with great tools for application management, and strong communication will reinforce their utility.

Step Four: Educate End Users and Keep Them in the Loop

Whether you’re preparing for a new macOS rollout two months in advance or two weeks in advance, you’ll need to let Apple device users on your network know what’s coming, why it matters, and what actions they’ll need to take.

While two weeks isn’t usually enough time to prepare for the changes a new operating system can bring, we recommend prioritizing clear messaging as soon as your team is able to coordinate sending relevant information to end users.

Communicate Early and Often: Make Sure Everyone’s on the Same Page

Whether you’re letting an end user know that you’ve been alerted to an incompatible application or you’re sending a message letting them know that they won’t be able to use certain applications on their company device until they’ve completed a required update, err on the side of giving advance notice.

Communicate directly with your end users about important changes and steps they need to take in order to avoid compatibility issues with a new OS. Tell them what’s going on, how it will impact their work, and why it’s important for their whole business community that they act.

Keeping end users in the loop will also help circumvent business continuity issues that can disrupt the day-to-day workings of your organization. Even better, the alerts you set up to help you monitor potential issues will help you collect the data you need to improve your end users’ experience and your environment’s security into the future.

 

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