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Trouble Upgrading to MacOS Monterey

I keep getting the same message “Installation cannot proceed because the installer is damaged. Redownload the installer and try again.” I have tried deleting the install file in the applications folder twice and redownloading on a normal boot up and three times on safe boot mode as was recommended in several help articles to no effect. I've also tried creating a bootable USB drive of Monterey and updating it through recovery mode, as well as doing SMC and PRAM resets and performing first aid on the drive I'm trying to install it on, all to no effect. I still get the same message from above.


I have a 2019 16” Macbook Pro i9 with 64GB of RAM, and nearly 1Tb(969GB) of free hard drive space. I updated BigSur fully to the latest update before trying to upgrade. Any insight or help would be greatly appreciated.

MacBook Pro 16″, macOS 11.5

Posted on Feb 12, 2022 4:34 PM

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Posted on Feb 13, 2022 12:59 AM

If you are using a VPN disable it for the download

Trash the existing installer in the Applications folder if it still exists.

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

Then download the installer again and try installing in Safe Mode

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Question marked as Top-ranking reply

Feb 13, 2022 12:59 AM in response to TLivingston42

If you are using a VPN disable it for the download

Trash the existing installer in the Applications folder if it still exists.

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

Then download the installer again and try installing in Safe Mode

Feb 12, 2022 4:53 PM in response to TLivingston42

Congratulations. You have done a lot of the right things. I have one question. Did you do your download via Wi-Fi? If so, that is very likely your problem. It is simply too slow for these very large files and data corruption often occurs. I suggest connecting to the modem with an Ethernet cable to do the next download and it should go smoothly. I hope the helps and good luck.

Trouble Upgrading to MacOS Monterey

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