At times, it can be difficult to determine what your options are for upgrading a given Mac. So, it’d be great to have someone who knows all the minutia and can guide you on the best path to take... a guide or sherpa. Or a chaperone!

Meet 'Mac Upgrade Chaperone' 🖥️🤵‍♂️ This script will guide you to the best (available) macOS upgrade method for a given Mac. Broadly, the upgrade methods range from 'best case scenario' (send an MDM command), through 'not so bad' (manual intervention needed e.g. not enough free space), to 'erase and re-install' (nuke & pave via EACS, MDM command, Recovery, depending on options), and the true dead-end scenario: this Mac cannot run the specified macOS version (e.g. incompatible).

• Check and report on which requirements are not met
• Determine the best method available, explain why, provide links to relevant Apple documentation
• Write two log files are written to disk (general log + error log)
• Display this guidance on-screen using AppleScript
  • Alternative: 'silent mode' doesn't display any notifications on-screen and only logs the results
• Jamf Pro extension attribute for reporting the MUC conclusion into Jamf Pro inventory, then create Smart Groups e.g. '✅ Ready to upgrade, '⚠️ Intervention needed' and '❌ Cannot upgrade'

1. Will this script download and install macOS? No.
   ------- Instead, check out s.u.p.e.r, nudge or mist
   Will this script determine what's possible and let you know? Yes.
   ------- This script provides advice only.
2. Is this still a work-in-progress? Yes!
   ------- If you have a suggestion on checks that should be included or false positives you notice, please let me know- submit a issue!

You can view example output of both logs here

• ✅ Is the Mac connected to a Wi-Fi network?
• ✅ Is the Mac connected to a wired network?
• ✅ Is apple.com:443 reachable and open?

• ✅ Is there an MDM profile?
• ✅ Is the MDM profile valid (ie not expired)?
• ✅ Is the MDM profile non-removable?
• ✅ Is the Push Certificate valid?
• ✅ Was the device enrolled via Automated Device Enrollment (aka DEP)?
• ✅ Was the device enrolled using User-Approved?
• ✅ Can we connect to the MDM server?
• ✅ Has a Bootstrap Token been escrowed to the MDM server?

MDM Deferrals/Restrictions

• Is there a deferral in place for macOS upgrades? If so, how many days?
• ✅ Is the Software Update Catalog URL set to Apple's default?

• ✅ Are the expected volume names found? (Macintosh HD, Macintosh HD - Data, Preboot, Recovery, VM)
• ✅ Is there enough available space?

• ✅ Is the Mac hardware compatible with $targetOS?
• ✅ Can we upgrade directly from the current installed macOS version?

• ✅ Is there a macOS installer applicaton on disk? "/Applications/Install $targetOS.app"
• ✅ Is the startosinstall binary available the installer too?

1. Upload script
2. Create policy (self service, ongoing, include an inventory update)
3. Upload extension attribute (optional)
4. Scope to your test device
5. Execute the script
6. Marvel at resulting files
7. Admire the info now available for scoping in Jamf Pro (if you used the extension attributes)

1. Download script
2. Execute sudo sh /path/to/muc.sh