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Casper - Upgrading Macs to latest operating system

Upgrading Macs to to the latest OS is a two-step process. Since the OS installers are several GB, it's recommended to cache them prior to installing, then using a second policy to run the cached installer.

Upgrading to macOS High Sierra

You will need to create two smart groups and two policies to upgrade machines to High Sierra.

Group 1: Eligible for High Sierra

  • Criteria - Operating System Version greater than or equal 10.8
  • Criteria - Operating System Version less than 10.13

Group 2: macOS High Sierra installer present

  • Criteria - Application Title is Install macOS High Sierra.app

Policy 1: Deploy the installer

  1. Create a new policy. Under General, set the trigger to Recurring Check-in, and set the execution frequency to Ongoing.
  2. Under Packages, add the 10.13.0 - Install macOS High Sierra.pkg package and leave the action set to Install.
  3. Under Scope > Targets, add the machines you'll want to upgrade or use the above created Eligible for High Sierra smart group.
  4. Under Scope > Exclusions, add the macOS High Sierra installer present smart group created above.
  5. Under Maintenance, make sure the Update inventory box is checked.
    • Result: The scoped machines will cache the installer the next time they check in (usually within 30 minutes).

Policy 2: Run the installer

  1. Create a second policy. This will run the pre-deployed installer, immediately restarting to begin the upgrade. Because this is immediate, it's recommended to only run this via Self Service.
  2. Under Scripts, add the 10.13 - Upgrade to High Sierra script.
  3. Under Self Service, check the Make available in Self Service box and the Feature the policy on the main page box.
  4. Under Self Service, it is recommended to add a description warning that it will instantly reboot, and checking the Ensure that users view the description checkbox.
  5. Set Scope to the above created smart group, macOS High Sierra installer present
  6. Optional: Under Scope > Limitations, add select authorized kerberos users or Moira groups. For example, you could set this to only desktop support technicians, so end users will not upgrade on their own accidentally.
  7. Note: Upon rebooting, you will need to enter the password of a FileVault-enabled user.

Upgrading to macOS Sierra

You will need to create two smart groups and two policies to upgrade machines to Sierra.

Group 1: macOS Sierra eligible

  • Criteria - Operating System Version greater than or equal 10.7.5
  • Criteria - Operating System Version less than 10.12

Group 2: macOS Sierra Cached

    • Criteria - WaitingRoomStatus is Install macOS Sierra 10.12.3.InstallESD.dmg

Policy 1: Cache the installer

  1. Create a new policy. Under General, set the trigger to Recurring Check-in, and set the execution frequency to Ongoing.
  2. Under Packages, add the Install macOS Sierra 10.12.3.InstallESD.dmg, and set the Action to Cache.
  3. Under Scope, add the machines you'll want to upgrade or use the above created macOS Sierra eligible smart group.
  4. Under Scope > Exclusions, add the macOS Sierra cached smart group
  5. Under Maintenance, make sure the Update inventory box is checked.
  6. Under Restart Options, click the - (minus) sign on the top right to remove the restart option. Otherwise the machine will reboot after caching!
    • Result: The scoped machines will then cache the installer the next time they check in (usually within 30 minutes). They will re-cache the installer whenever it is removed.

Policy 2: Run the installer

  1. Create a second policy. This will run the pre-cached installer, then immediately restart and begin the upgrade. Because this is immediate, it's recommended to only run this via Self Service.
  2. Under Packages, add the Install macOS Sierra 10.12.3.InstallESD.dmg package and set the Action to Install Cached.
  3. Scroll down on the left to the Restart Options, set the Startup Disk to OS X Installer, and set the Delay to 0 minutes or whatever delay you prefer. If your machines are encrypted you must check the box for Perform authenticated restart on computers with FileVault 2 enabled.
  4. Under Self Service, check the Make available in Self Service box and the Feature the policy on the main page box.
  5. Under User Interaction, you may want to add a note to the user in the Restart Message field
  6. Set Scope to the above created smart group macOS Sierra Cached.

Note: The caching policy must be given time to complete before running the installation policy, or the latter will fail.

Contact

  • If you need assistance creating policies or have any questions, please contact the Endpoint Management team at endpointmanagement@mit.edu.

IS&T Contributions

Documentation and information provided by IS&T staff members


Last Modified:

October 16, 2017

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