How to Upgrade to macOS Monterey

Written by Nathaniel Strauss

Last published at: May 10th, 2022
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Compatibility Notice

Mitel Connect is not compatible with Monterey. If you need to use Mitel Connect, do not upgrade at this time. A new version of Mitel Connect is scheduled to be available in early 2022.

It's important your Mac stay updated to the latest operating system supported by the district. 

  • Software compatibility. Ensure all software used for class works as expected. 
  • Security. Apple constantly releases new security patches to keep you safe. 
  • Features. Each OS release offers new features and performance improvements.

Installation requirements:

  • At least 26 GB disk space free. 
  • Mac plugged into power. 
  • All applications closed.

The upgrade will take about 1-2 hours to complete. During this time you will not be able to use your Mac. If the install fails at any point, restart your Mac and try to upgrade again from Self Service.

Upgrading at Home

The macOS Monterey installer is about 12 GB. Note if your home Internet plan has a data cap or bandwidth limits it may be difficult to to upgrade.

You will possibly need to free up disk space in order to complete the upgrade. Common places to delete files from include...

  1. Applications. Large unused Applications like iMovie, GarageBand, Keynote, Pages, Numbers, etc. Note: most users do not have permissions to remove Applications themselves. Open a help desk ticket by emailing helpdesk@shakopee.k12.mn.us
  2.  User home folder. Desktop, Documents, Downloads. Delete files or move to Google Drive.
  3. Other application support and cache folders. Primarily ~/Library/Application Support for apps which are no longer installed.

If you have any concerns about being able to upgrade from home or freeing up disk space please open a help desk ticket by emailing helpdesk@shakopee.k12.mn.us

Follow the directions below to complete the upgrade.

1. Open Self Service and sign in with your school credentials.

2. Before continuing make sure your Mac meets the installation requirements:

  • Ensure all work is saved and apps have been completely closed.
  • Be sure your Mac is plugged into power.
  • Mac has at least 26 GB disk space free.


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Freeing up disk space

One common barrier for installing MacBook updates is a lack of space. This is especially true on older devices. To help with this, we have increased our options in Self Service for uninstalling larger programs. Once an update is completed, you can reinstall these programs.

Uninstallers are available for:

  • Garageband
  • iMovie
  • Microsoft Office Applications (all except Outlook)

If you need assistance freeing up additional disk space please contact the help desk (helpdesk@shakopee.k12.mn.us).


3. Search for Monterey in the search bar and select Upgrade to macOS Monterey.

4. On newer model Macs you may be prompted to enter your password. This is a requirement and must be the same password you use to log into your Mac.

5. The macOS Monterey installer will be downloaded. This file is about 12 GB and usually takes between 20-45 minutes to download. If you are on a slower wireless connection it may take longer.

6. If your Mac does not meet the upgrade requirements you will see an error message. Make sure your Mac is plugged into power and has at least 26 GB of disk space free. If you receive an error message multiple times in a row, restart your Mac and try to upgrade again.

For additional help please contact the help desk (helpdesk@shakopee.k12.mn.us).

7. Once the installer successfully downloads it will prepare your Mac to upgrade and automatically reboot to complete the install process.

8. The actual install takes about an hour. Once completed your Mac will boot up and you can log in again. There is an additional 10-15 minutes of additional install time after the first login.