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Left iMac upgrading from Big Sur to Monterey overnight and it is stuck in reboot cycle unless I boot in Safe mode

When I leave my iMac to reboot as normal, it crashes and then immediately reboots. So I'm stuck in this cycle.


When I reboot in Safe mode then the iMac boots into Monterey.


Anything to look for when in Safe mode to fix this issue?

iMac Line (2012 and Later)

Posted on Dec 3, 2021 10:20 AM

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12 replies

Dec 4, 2021 4:00 AM in response to ksaro1

Since the mac is crashing even before the login window shows up, this suggests that one of two kinds of things is causing the problem:


  • either a launch daemon
  • or a kernel (or system) extension


Those are loaded before any user login; launch agents only run when there is a user logged in, and user launch agents are for one particular user.


I forgot to mention extensions earlier; in this case, it seems more likely that some extension is behind this.


Kernel Extensions are in /System/Library/Extensions or /Library/Extensions.


What is in there?


Dec 12, 2021 10:24 AM in response to Luis Sequeira1

Luis - thanks for the tips. I removed all 3rd party extensions and the iMac still crashed. I then erased the disk and installed Monterey from the internet when in the Recovery mode. I then used the Migration Tool to migrate from my last full backup. (I migrated All, not just the user accounts) FWIW - when in Safe mode I couldn't access the camera. Nor did X11 work. I don't know if that is normal or not?


I can now boot. However, there are still some issues.

1) I can't access the Security & Privacy nor the Notifications & Focus panes from the System Preferences main pane.

2) I also seem to have lost the photo that goes with my Apple ID? There should be a photo showing for my Apple ID account. (This worked prior to Monterey)


3) Also, the Screen Saver lets me use a folder for the screen saver pictures (as I had in all previous versions of Mac OS). However, I just get a black screen shown as Preview and when the iMac goes into screen saver mode.

Dec 4, 2021 2:17 AM in response to Luis Sequeira1

Luis Sequeira1 wrote:

In addition to the login items, post the contents of the following folders:

/Library/LaunchDaemons
/Library/LaunchAgents
~/Library/LaunchAgents

To open each of the above folders, press Command-Shift-G in the Finder, and then paste the respective line, and press enter.

Then post the contents here.

I removed all login items as requested and I still get a crash on reboot.


The contents of the requested directories are as follows:


$ ls -larth /Library/LaunchAgents 

total 72

-rw-r--r--  1 root wheel  626B 1 Jan 2001 org.chromium.chromoting.plist

-rw-r--r--  1 root wheel  523B 29 Mar 2019 com.microsoft.OneDriveStandaloneUpdater.plist

lrwxr-xr-x  1 root wheel  104B 14 Oct 2019 com.oracle.java.Java-Updater.plist -> /Library/Internet Plug-Ins/JavaAppletPlugin.plugin/Contents/Resources/com.oracle.java.Java-Updater.plist

-rw-r--r--  1 root wheel  515B 16 Oct 2020 com.box.desktop.helper.plist

-rw-r--r--  1 root admin  632B 11 Dec 2020 org.macports.startx.plist

-rw-r--r--  1 root wheel  693B 25 Apr 2021 org.xquartz.startx.plist

-rw-r--r--@ 1 root wheel  799B 23 Aug 19:42 com.google.keystone.agent.plist

-rw-r--r--@ 1 root wheel  907B 23 Aug 19:42 com.google.keystone.xpcservice.plist

-rw-r--r--  1 root wheel  577B 11 Sep 00:52 com.adobe.ARMDCHelper.cc24aef4a1b90ed56a725c38014c95072f92651fb65e1bf9c8e43c37a23d420d.plist

-rw-r--r--  1 root wheel  405B 2 Dec 18:11 com.microsoft.update.agent.plist

drwxr-xr-x 12 root wheel  384B 3 Dec 12:46 .

drwxr-xr-x 71 root wheel  2.2K 3 Dec 15:45 ..

$ ls -larth /Library/LaunchDaemons 

total 144

-rw-------  1 root wheel  288B 19 Dec 2018 com.microsoft.OneDriveUpdaterDaemon.plist

-rw-r--r--  1 root wheel  382B 27 Dec 2018 org.wireshark.ChmodBPF.plist

-rw-r--r--  1 root wheel  824B 29 Mar 2019 com.microsoft.OneDriveStandaloneUpdaterDaemon.plist

-rw-r--r--  1 root wheel  833B 25 May 2019 jp.co.canon.MasterInstaller.plist

-rw-r--r--  1 root wheel  632B 19 Sep 2019 com.apple.installer.osmessagetracing.plist

-rw-r--r--  1 root wheel  580B 3 Oct 2019 jp.co.canon.cnwidadrHelperTool.plist

-rw-r--r--  1 root wheel  559B 10 Oct 2019 com.apple.serverd.plist

lrwxr-xr-x  1 root wheel  103B 14 Oct 2019 com.oracle.java.Helper-Tool.plist -> /Library/Internet Plug-Ins/JavaAppletPlugin.plugin/Contents/Resources/com.oracle.java.Helper-Tool.plist

-rw-r--r--  1 root wheel  1.0K 22 Nov 2019 com.bearisdriving.BGM.XPCHelper.plist

-rw-------  1 root wheel  271B 17 Mar 2020 com.microsoft.teams.TeamsUpdaterDaemon.plist

-rw-r--r--  1 root wheel  903B 3 May 2020 org.serviio.server.plist

-rw-r--r--  1 root wheel  515B 16 Oct 2020 com.box.desktop.autoupdater.plist

-rw-r--r--  1 root admin  638B 11 Dec 2020 org.macports.privileged_startx.plist

-rw-r--r--  1 root wheel  633B 25 Apr 2021 org.xquartz.privileged_startx.plist

-rw-r--r--  1 root wheel  707B 5 May 2021 com.bombich.ccchelper.plist

-rw-r--r--  1 root wheel  486B 11 Aug 12:50 com.adobe.ARMDC.SMJobBlessHelper.plist

-rw-r--r--  1 root wheel  474B 11 Aug 12:50 com.adobe.ARMDC.Communicator.plist

-rw-r--r--@ 1 root wheel  828B 23 Aug 19:42 com.google.keystone.daemon.plist

-rw-r--r--  1 root wheel  428B 2 Dec 18:11 com.microsoft.autoupdate.helper.plist

drwxr-xr-x 21 root wheel  672B 3 Dec 12:51 .

drwxr-xr-x 71 root wheel  2.2K 3 Dec 15:45 ..

$ ls -larth ~/Library/LaunchAgents

total 24

-rw-r--r--  1 ksaro1 staff  688B 4 Apr 2021 homebrew.mxcl.unbound.plist

-rw-r--r--  1 ksaro1 staff  686B 30 Sep 09:21 com.dropbox.DropboxMacUpdate.agent.plist

-rw-r--r--@  1 ksaro1 staff  1.1K 2 Dec 18:04 com.google.Chrome.framework.plist

drwxr-xr-x@  5 ksaro1 staff  160B 2 Dec 18:04 .

drwx------@ 102 ksaro1 staff  3.2K 4 Dec 09:53 ..


I do have Xcode installed and I notice that its update is hanging too. When I go to App Store it shows the clock for the update's download at about 11:00 and it stays there for at least 1 day now.


I also have 2 user accounts set up on my iMac. So when you mention ~, which account would I use? One or both? And when the iMac boots which account is used? I'm normally given a screen with both accounts shown and I have to choose which one to login in to. My iMac is crashing before this screen ever comes up.

Dec 4, 2021 6:09 AM in response to ksaro1

In /Library/Extensions, everything that does not have an Oct 18 date comes from your previous installation.

Those with Oct 18 are part of the Monterey install.


In particular, this comes from as far back as 2013:


drwxr-xr-x 3 root wheel 96B 14 Aug 2013 hp_io_enabler_compound.kext



This is from 2016:


drwxr-xr-x 3 root wheel 96B 16 Aug 2016 TruStudioPCUSBAudioPlugin.kext



And there are also these:


drwxr-xr-x@ 3 root wheel 96B 19 Mar 2019 AppleMobileDevice.kext

drwxr-xr-x 3 root wheel 96B 11 Sep 2019 SATSMARTLib.plugin

drwxr-xr-x 3 root wheel 96B 11 Sep 2019 SATSMARTDriver.kext



You could try deleting stuff, but I suggest a different approach.


You still have a backup from before installing Monterey, right?


I suggest you erase, install Monterey and then migrate ONLY the user accounts.

This is the best thing to do when upgrading to a new OS, anyway.


Dec 14, 2021 3:32 AM in response to ksaro1

Ok, adding a photo to the Apple ID has a bug. When I added a photo, this added photo was also overwritten as my own account on the iMac's photo. I had to go in to System Preferences => Users & Groups and change my account's photo back to the original one.


Also, for both Apple ID and the user accounts, why can't we search folders for photos? I can't recall on past versions of the OS, but I'm pretty sure you could, as my original account's photo isn't in the list of photos I can search in Monterey. You can search folders for wallpaper photos, so why not for account photos?

Left iMac upgrading from Big Sur to Monterey overnight and it is stuck in reboot cycle unless I boot in Safe mode

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