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Upgrade to Monterey not completing

Hi folks!


I’ve been trying to upgrade my MacBook Pro (13”, 2020) to Monterey, using an installer provided by my company’s IT organization. The initial part of the upgrade seems to go well, but when it comes time to restart the laptop, the restart hangs. The screen only shows the pointer, and the laptop never restarts. If I force it to restart with the power button, it simply boots into MacOS 11.6.3 (the pre-upgrade version of the OS). If I run the installer again, the whole process repeats.


Does anyone have any suggestions on how to get the installation to complete?


Thanks!

MacBook Pro (2020 and later)

Posted on Jan 27, 2022 6:12 PM

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Question marked as Top-ranking reply

Posted on Jan 28, 2022 10:18 AM

Try to do the install from Safe Mode as lllaass suggested previously. I've had better luck from the Safe Mode because I evidently have some 3rd party software that interferes with the installation so try the following:

#1 - boot into Safe Mode according to Start up your Mac in safe mode - Apple Support.

NOTE: Safe Mode boot can take up to 3-5 minutes as it's doing the following; 
• Verifies your startup disk and attempts to repair directory issues, if needed
• Loads only required kernel extensions (prevents 3rd party kernel/extensions from loading)
• Prevents Startup Items and Login Items from opening automatically
• Disables user-installed fonts 
• Deletes font caches, kernel cache, and other system cache files

#2 - go to the System/Software Update preference pane and begin the download.

#3 - run the installer from the Safe Mode.




5 replies
Question marked as Top-ranking reply

Jan 28, 2022 10:18 AM in response to Cricket Liu

Try to do the install from Safe Mode as lllaass suggested previously. I've had better luck from the Safe Mode because I evidently have some 3rd party software that interferes with the installation so try the following:

#1 - boot into Safe Mode according to Start up your Mac in safe mode - Apple Support.

NOTE: Safe Mode boot can take up to 3-5 minutes as it's doing the following; 
• Verifies your startup disk and attempts to repair directory issues, if needed
• Loads only required kernel extensions (prevents 3rd party kernel/extensions from loading)
• Prevents Startup Items and Login Items from opening automatically
• Disables user-installed fonts 
• Deletes font caches, kernel cache, and other system cache files

#2 - go to the System/Software Update preference pane and begin the download.

#3 - run the installer from the Safe Mode.




Jan 28, 2022 1:42 AM in response to Cricket Liu

Try booting to Safe Mode. That boot up takes minutes and clears caches and other things that may resolve your problem.

How to use safe mode on your Mac - Apple Support

Try installing when in Safe Mode


Do you have enough free disk space?

If upgrading from macOS Sierra or later, your Mac needs 26GB of available storage to upgrade.


Also uninstall any antivirus, internet security or "cleaning" apps before trying installing again.


Are you using File Vault to encrypt the disk? If so turn it off and then try after the de-encrypting is complete. That can take many hours.



Have you installed upgrade before using an installer provided by your employer? Are you connected to the internet when upgrading?

Jan 28, 2022 2:44 AM in response to Cricket Liu

Cricket Liu wrote:

Hi folks!

I’ve been trying to upgrade my MacBook Pro (13”, 2020) to Monterey, using an installer provided by my company’s IT organization. The initial part of the upgrade seems to go well, but when it comes time to restart the laptop, the restart hangs. The screen only shows the pointer, and the laptop never restarts. If I force it to restart with the power button, it simply boots into MacOS 11.6.3 (the pre-upgrade version of the OS). If I run the installer again, the whole process repeats.

Does anyone have any suggestions on how to get the installation to complete?

Thanks!

Follow suggestions and guidance from previous posting first.


Verify with your employer / IT Department where exactly did they get this " Installer "


For information purposes - the Full Version of macOS Monterey 12.2 is approximately 12.2 GB in size ( yes, not a typo regarding size )

Jan 28, 2022 12:21 PM in response to Old Toad

Thanks very much for the suggestion! I had booted into Safe Mode before but the installer didn't complete--it reported that it couldn't reach a server, if I remember correctly. I should have looked into that more carefully.


This time, I booted into Safe Mode and found that a piece of security software I use had left the resolver configuration pointed at the loopback address. In Safe Mode, though, the DNS server itself doesn't start, so all name resolution was failing. Once I fixed the resolver configuration, the installer ran fine. My MacBook is now running 12.2.


You'd think I might be qualified to diagnose a DNS problem, but apparently not!


I still don't know what prevented the installation from completing when booted normally, but Safe Mode would have worked right away if not for the security software. (Bug filed, by the way.)

Upgrade to Monterey not completing

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