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Tuesday saw Apple drop the first public release of macOS Catalina, a move which has caught out a number of developers, including some offering security solutions, as well as organizations and ordinary macOS users. While SentinelOne is already Catalina-compatible (more details below), Apple’s unannounced release date has left some scrambling to catch up as macOS 10.15 introduces some major changes under the hood, undoubtedly the biggest we’ve seen in some time. Anyone considering a Catalina upgrade should be aware of how these changes could affect current enterprise workflows, whether further updates for dependency code are required and are available, and whether the new version of macOS is going to necessitate a shift to new software or working practices. In this post, we cover the major changes and challenges that Catalina brings to enterprise macOS fleets.

Does SentinelOne Work With macOS Catalina?

First things first: Yes, it does. SentinelOne macOS Agent version 3.2.1.2800 was rolled out on the same day that Apple released macOS 10.15 Catalina. This Agent is supported with Management Consoles Grand Canyon & Houston. Ideally, you should update your SentinelOne Agent version before updating to Catalina to ensure the smoothest upgrade flow.

Developers Play Catalina Catch-up

Contrary to popular (mis)belief, kexts or kernel extensions are still alive and well in Catalina, and the move to a new “kextless” future with Apple’s SystemExtensions framework remains optional at least for the time being. However, that doesn’t mean your current array of kernel extensions from other developers are necessarily going to be unproblematic during an upgrade.

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New rules for kexts mean developers at a minimum have to notarize them, and users will have to restart the Mac after approving them. On top of that, developers – particularly those distributing security software – will need to update their kexts and solutions to be compatible with Catalina’s new TCC and user privacy rules, changes in partition architecture and discontinued support for 32-bit apps (see below), among other things.

Upgrading a Mac to 10.15 with incompatible kexts already installed could lead to one or more kernel panics.

The safest bet is to contact vendors to check on their Catalina support before you pull the trigger on the Catalina upgrade. If for some reason that’s not possible or you have legacy kexts installed which are out of support, the best advice is to remove those before you upgrade a test machine, then immediately test for compatibility as part of your post-install routine.

Bye Bye, 32-Bit Applications

Apple called time on 32-bit applicationsseveral releases ago, offering increasingly urgent warnings of their impending doom through High Sierra and Mojave. However, in macOS Mojave these would still run after users dismissed the one-time warning alert, but Catalina finally drops the axe on 32-bit applications.

Before upgrading, check what legacy applications you have installed. From the command line, you can output a report with:

system_profiler SPLegacySoftwareDataType

For GUI users, you can take a trip to Apple > About This Mac and click the System Report… button.

Scroll down the sidebar to “Legacy Apps” and click on it. Here you’ll see a list of all the apps that won’t run on Catalina. macOS 10.15 itself will also list any legacy apps during the upgrade process, but it’s wise to be prepared before you get that far.

VPP & Apple School/Business Manager Support

Catalina continues to allow various enterprise upgrade paths through its Mobile Device Management (MDM) framework, Device Enrollment Program (DEP) and Apple Configurator. For organizations enrolled in Apple’s Volume Purchase Program or with Apple Business Manager or Apple School Manager licensing, Catalina is supported right out of the door, saving you the bother of having to manually download, package and then install multiple instances of 10.15.

New in Catalina are Managed Apple IDs for Business, which attempt to separate the user’s work identity from their personal identity, allowing them to use separate accounts for things like iCloud Notes, iCloud Drive, Mail, Contacts and other services.

There is a plus here for user privacy, but for admins used to having total control over managed endpoints, be aware that a device with an enrollment profile and managed Apple ID means the business loses power over things like remote wipe and access to certain user data. Effectively, the device is separated in to “personal” and “managed” (i.e., business use), with a separate APFS volume for the managed accounts, apps and data.

Privacy Controls Reach New Heights

That’s not the only thing to be aware of with regards user data. The biggest change that end users are going to notice as they get to work on a newly upgraded macOS 10.15 Catalina install is Apple’s extended privacy control policies, which will manifest themselves in a number of ways.

In the earlier, macOS 10.14 Mojave, there are 12 items listed in the Privacy tab of the Security & Privacy pane in System Preferences. Catalina adds five more, with Speech Recognition, Input Monitoring, Files and Folders, Screen Recording, and Developer Tools added in the new version of macOS.

Here’s what the first three control:

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Importantly, the three items above can only be allowed at the specific time when applications try to touch any of these services. Although applications can be pre-denied by MDM provisioning and configuration profiles, they cannot be pre-allowed. That has important implications for your workflows since any software in the enterprise that requires these permissions must obtain user approval in the UI in order to function correctly, or indeed at all. Be aware that Catalina’s implementation of Transparency, Consent and Control is not particularly forthcoming with feedback. Applications may simply silently fail when permission is denied.

The most obvious, but certainly not only, place where privacy controls are going to cause issue is with video meeting/conferencing software like Zoom, Skype and similar. Prompts from the OS that suggest applications must be restarted after permission has been granted for certain services like Screen Recording have raised fears that clicking ‘Allow’ during a meeting might kick users out of the conference while the app re-launches. Conversely, users who inadvertently click ‘Don’t Allow’ may wonder why later attempts to use the software continue to fail. Civ 4 windows 10 fix.

What all this means is that with macOS Catalina, there is a greater onus on sysadmins to engage in user education to preempt these kinds of issues before they arise. Thoroughly test how the apps you rely on are going to behave and what workflow users need to follow to ensure minimal interruption to their daily activities.

The remaining two additional items are:

These last two can both be pre-approved. The first grants access to user files in places like Desktop, Downloads, and Documents folders. The second allows developers to run their own software that isn’t yet notarized, signed or ready to be distributed (and thus