Issue
Whenever the user tries to run an operating system update from Software Update, the update will begin downloading and then show the error message:
Failed to personalize the software update. Please try again.
Environment
Managed macOS laptop
Description
(paraphrased from a customer's voicemail by the technician handling the issue)
Today you contacted the Technology Service Desk to receive help with your managed device prompting for an OS software update. But when the prompt is clicked and the software tries to update it shows an "Failed to personalize the software update. Please try again." error.
We decided that the best course of action was to try again after a device restart and ensure that the internet was connected but each time the same error appeared.
Resolution
If restarting your computer does not solve this issue, please reach out to your regional support unit. They can follow these troubleshooting steps in this rough order:
- Verify that ussadmin has Secure Token.
- Boot the device to Safe Mode and retry the software update.
- Verify that the any Ethernet adapters being used are known good adapters and that there are no ongoing network outages.
- Create a new temporary admin account and try running the update from there.
- Back up the device and re-install the OS from macOS recovery.
- If that does not work, enter DFU mode via Apple Configurator and restore the machine. This is often how far you will need to go to fix the issue.
- Once all steps have been taken, reach out to Apple Support.