6 Facts Admins Should Know About macOS Monterey 12.3

Written by Ashley Gwilliam on March 21, 2022

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This article was inspired by a webinar featuring Apple experts Tom Bridge and Bradley Chambers. Tom is JumpCloud’s Principal Product Manager and Bradley is Cribl’s Senior Digital and Web Marketing Manager. JumpCloud IT columnist Pam Lefkowitz served as the webinar’s moderator.

It’s that time again.

Flowers are blooming, days are getting longer, and Apple released (on March 14) its macOS spring update: macOS Monterey 12.3.

IT admins and developers have an opportunity to play with the pre-release ahead of time. If you have yet to test pre-leases in your work environment, visit AppleSeed for IT to get started. 

AppleSeed for IT is a public program for IT professionals and technology managers wanting to experiment with pre-releases of iOS, iPadOS, macOS, tvOS, and watchOS throughout the year. If you already have the macOS public beta installed, select System Preferences > Software Updates to download the most current beta. 

Friendly Tip: always maintain a workstation on the most current beta. Ideally, you want to be “living in” the software to stay on top of upcoming changes and stay on your IT game. 

With that said, pre-release software can contain bugs that negatively affect the performance of apps, battery life, and overall speed. So, steer away from completely switching to beta on standard organizational devices. 

In this article, we’ll discuss how to leverage the update’s new features to optimize your organization’s IT strategy, how to avoid potential conflicts, and more. Here’s a quick look at Monterey 12.3’s new features: 


macOS Monterey 12.3: New Features 

We’ve got some completely new features and a few others moving from beta to public:

  • New Focus Modes
  • Universal Control
  • New Emojis 
  • “Hide My Email” 
  • iCloud Private Relay
  • Live Text
  • FaceTime Extensions 
  • Expanded Shortcuts on MacOS
  • Apple Configurator for iOS
  • Erase All Contents and Settings (EACS)
  • Increased Security Around Authentication 

During Apple’s previous release, our team was most impressed by Focus Mode

The functionality allows users to create customizable focus modes that filter out notifications for work, personal life, and more. From an end-user perspective, the new ability to sync focus modes across multiple devices has been a game-changer. 

Our Mac computers, iPhones, and tablets can now exist in harmony — ommm. This time, our favorite feature is a tie between Universal Control and Erase All Contents and Settings (EACS). 

Let’s dive into some of the changes most likely to impact your workflow. 


1. Say Goodbye to Python 2.7

Undoubtedly, one of Monterey’s most impactful changes is its removal of Python 2.7. Run a python command post-update, and you will receive an error message. 

Translation: Apple is no longer responsible for any version of Python. If your IT department relies on Python 3, you must either a) ensure you have Xcode Developer Tools installed or b) update your paths to include whichever relocatable Python framework they have installed. 

The good news? You don’t have to deploy the update for employees immediately. Utilizing the newest version of macOS is alway the most secure course of action. But it shouldn’t be done at the expense of running into unexpected bottlenecks. 

Take a couple weeks to prepare behind the scenes, if needed. In summary, update your tooling to continue using your own version of Python. 


2. Evaluate iCloud Private Relay

Some of Monterey’s recent features are most “fun” from a user perspective. But, as an admin, you may be wondering: would I ever want to turn off iCloud Private Relay? 

As with many IT scenarios, the answer depends on what you’re trying to do. The VPN-like nature of iCloud Private Relay has proven extremely useful for millions of Apple users. For example, say a user is working remotely via a hotel, coffee shop, or suspicious network. 

As long as they activate Private Relay in their iCloud settings, they can rest assured their browsing history and IP address will remain hidden from the network. The built-in capability sends user data through a pair of relays. The result? Apple knows the user’s real IP, but not their DNS request; and the proxy knows the user’s DNS request, but not their real IP address. 

Unfortunately, Private Relay lacks the versatility and power needed by most corporate IT departments. It may even cause some of their applications to act a bit wonky. In addition, organizations may wish to restrict the feature for compliance, disclosure, and company policy reasons. 


3. Erase All Contents And Settings (EACS) is Here

EACS provides admins with a convenient option for restoring properly-equipped Mac computers to Setup Assistant. The feature has been in Beta until now. The cool thing about EACS is that it removes all user data in 5 minutes or less! Here’s how IT expert Tom Bridge describes the grim reality for admins using Obliteration Mode before EACS. 


“Either there are no bootstrap tokens on the device if it’s firewall encrypted, but what you have at that point, when the system receives an erasure command, which says, ‘Im done here, please reset for the next person.’” Bridge said. “What happens is the system says, ‘Cool,’ or ‘I could not go through the EACS environment.”


Firing an eraser command prior to iOS12 didn’t just erase user data and start over. It actually wiped out the entire disk including the operating system. In other words, it stripped the volume encryption tools from the system. 

Previously, your only option was to go into the recovery web or retrieve the recovery partition version, before reinstalling the operating system. The ordeal took a yawn-worth amount of time. 


4. Sync Your Device Control with Universal Control

Have you ever wished you could execute the same actions across multiple devices without a second keyboard, trackpad, and mouse? Well, now you can. 

Monterey 12.3 allows users to connect devices which are signed into the same AppleID. This feature allows for greater convenience, flexibility, and control for those working from multiple devices simultaneously. For example, a Web designer could design a graphic via pencil on an iPad, and watch it come to life on his Macbook. 

Universal Control copies and pastes actions directly between logged on machines, using existing WiFi and bluetooth technologies, as well as provides keyboard and mouse control for an iPad as an extension of the Mac. This fascinating experience provides interesting opportunities for collaboration and shared experiences. 


“For example, say you’ve got four laptops on a table, and you’re troubleshooting different devices,” IT expert Bradley Chambers said. “On the same Apple ID, you could force Universal Control on the machines around you. Museums could potentially use the feature with kiosk systems for iPads. There are a lot of opportunities for Apple to evolve from a business perspective.” 


It’s worth mentioning that Universal Control only works with up to three devices right now. But the fact that it utilizes Airdrop to eliminate the need for file sharing is pretty groundbreaking. 


5. File Sharing Apps Might be Affected 

Does anyone on your team rely heavily on Dropbox for file sharing? How about Microsoft OneDrive? If so, they might encounter some issues with Monterey 12.3. 

The update is deprecating Cloud File APIs used by both apps to download files on demand. These APIs enable cloud-stored files to be available when you need them, without taking up space when you don’t. With that said, both Dropbox and Microsoft have updates currently in beta. 


“The cool thing is it looks like major vendors are not going to stop working completely,” Bridge said. “Folders will still sync. There might be issues where files are showing up in Finder but not taking up hard drive space though.” 


Of course, if the majority of your organization’s files are accessible in the cloud via Google Drive, you’re golden. Bridge said this file-sharing snafu provides good motivation to embrace cloud-based workflows. The more tools that are accessible via web browser, the less obstacles your team will encounter during an update. 


6. Shortcuts are Expanding 

Another impactful change with Monterey 12.3 is the added availability of macOS shortcuts. Apple now boasts a gallery of pre-built shortcuts via its Shortcuts App. The functionality is integrated throughout macOS for running shortcuts from the menu bar, Finder, Spotlight, Siri, and more.


“One of the things I was most excited to see in Apple’s documentation for shortcuts was how you use things on post APIs and get APIs to interact with shortcuts to do tasks,” Bridge said. “As an admin, you can interact directly with the JumpCloud API using shortcuts on your device.”


JumpCloud allows users to use a restful API to obtain API tokens for their instances. For example, say you want to identify organizational users with older devices that don’t support Monterey 12.3. Just slap your tokens into queries via Shortcut to retrieve a list. 


Our macOS Features Wish List

While we’re impressed with Apple’s macOS Monterey updates overall, the webinar discussion generated a few “wish list” items. Below are some of the iOS capabilities we would love to see:

  • Superior deferral controls: Wouldn’t it be cool if the deferral controls on the install were more versatile? Though Apple is making strides, the operating system’s deferral functionality isn’t at peak convenience levels yet. 
  • “Clone” settings: We’re not sure how Apple would pull this off, but we’d appreciate another option besides EACS. For example, say an employee returns a used device. Instead of restoring it to original factory settings, the organization chooses to return the device to a preformulated setting for menu bars, wallpaper, etc. 
  • Greater MDM specifications: The landscape for handling patch management on iOS devices is more complicated than it is for Macbooks. But we hope Apple gives MDM more attention in the near future. 


Improve IT Efficiency with macOS Monterey 12.3 

Undoubtedly, OS updates can be stressful. The good news is we don’t see anything likely to incite behemoth roadblocks at this time. Admins will likely enjoy the enhanced convenience provided by capabilities like EACS, Universal Control, and Shortcuts. 

Got more questions about Monterey 12.3? 

Watch the webinar for additional helpful tips. 

Ashley Gwilliam

Ashley Gwilliam is a Content Writer for JumpCloud. After graduating with a degree in print-journalism, Ashley’s storytelling skills took her from on-camera acting to interviewing NBA basketball players to ghostwriting for CEOs. Today she writes about tech, startups, and remote work. In her analog life, she is on a quest to find the world's best tacos.

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