Monterey installation issues

I am currently on my 3rd download of Monterey. The first errored after completing the download stating I needed additional files. It then downloaded Big Sur 11.6.. Went through the download for the second time and it errored again stating that critical files were missing, then downloaded additional updates (5 minute download). Currently on my third try. 2019 MBP 16". Anyone else having issues simian and have a solution? I am afraid I am in an endless cycle here.

MacBook Pro with Touch Bar

Posted on Oct 27, 2021 9:48 AM

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6 replies

Oct 27, 2021 11:39 AM in response to tmsmedic

tmsmedic wrote:

I am currently on my 3rd download of Monterey. The first errored after completing the download stating I needed additional files.

It then downloaded Big Sur 11.6.. Went through the download for the second time and it errored again stating that critical files were missing, then downloaded additional updates (5 minute download). Currently on my third try. 2019 MBP 16".

Anyone else having issues simian and have a solution?


This is the first error of this sort I have seen...Verify you are logged into an Admin user account.


If your download speed is suspect get on a faster Network.

Never had an issue with Wi-Fi and running the macOS upgrades for at least a decade.

I have the same 16" MBP 2019 with no issue from Big Sur to Monterey.


You might want to look at your Security settings....and make a change(?)



About Startup Security Utility\

https://support.apple.com/en-us/HT208198

Oct 27, 2021 11:48 AM in response to tmsmedic

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.


Oct 27, 2021 11:16 AM in response to tmsmedic

I may be able to help. I am a strong advocate of not using Wi-Fi for downloading OS updates and upgrades. These files are simply too large and Wi-Fi is often too slow. (Not for everyone, though.) Then corruption occurs and the file cannot install. Instead. I recommend that for OS installs you use a wired Ethernet connection. That usually solves the problem. Maybe you will have to temporarily move the computer. If that can't be done, then you will have to endure a number of very lengthy downloads until you get a clean one that will install. Good luck.

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Monterey installation issues

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