Why can't I upgrade from Catalina to Monterey? Should I upgrade to Big Sur prior to that?

In Theory one can jump directly from a Fully Updated version of Catalina to Monterey and bypass Big Sur.

As previous posting mentions, there have been issues for some ( not all ) who attempt the Jump.

January 9  2022 Version # 3

The below points should be consider before attempting the upgrade.

Point # 1 - Does the >>  Computer Qualify for the Monterey upgrade 

Point # 1A - There are reports appearing on the ASC Forums regarding failed installation of Monterey on older Qualifying Apple Computers. In most cases this is related to having a NON Apple Original internal drive ?  

The EFI Boot ROM included in Monterey is verifying for Original Apple Drive and if not found , may Balk or fail to upgrade to Monterey. 

Reports indicate the EFI BOOT ROM is Required to Flash the Computer and is a  requirement for a Successful Monterey Installation.

The workaround is to flip out the Replacement Drive and put the Apple Original Drive in. Run the Monterey Installer to that drive. Then reverse the above procedure and run the Monterey Installer to the After Market drive.

Credit for above workaround belongs to previous person posting on this question.

Point # 2- >> How to upgrade to macOS Monterey

Point # 3 - Empty Space Requirements  >> If upgrading from macOS Sierra or later, your Mac needs 26GB of available storage to upgrade. If upgrading from an earlier release, your Mac needs up to 44GB of available storage. 

Point # 4 - Empty Space afterwards - it is suggested to keep at least 15% of the Drive Total Capacity as Empty Space for good operations of the computer and for additional updates to Monterey to download, expand and install.

Point # 5 - The upgrade will require a quick, stable and reliable Internet Connection - preferred method is via Ethernet Connection. 

Point # 6 - If using Wifi - move computer as close to the Access Point / Router and disconnect all other devices connected to Wifi. Want the maximum bandwidth for the computer being upgraded to Monterey

Point # 7 - Commercial VPNs should only be used if Mandated by Corporate Head Office for working remotely. Otherwise - ones Privacy and Security touted by the VPN is suspect. 

Point # 8 - If downloading Monterey from behind a VPN it may increase Packet Looses and an incomplete or corrupted Installer.

Point # 9 - AntiVirus Software should be removed as per Developers Instructions. They are unneeded, cause havoc and interfere with the normal operation of the OS including the download and installation of Monterey. 

The Built in Security  is all that is required. 

There are no known Windows-like Viruses in the wild that self replicate and affect macOS because of the underling UNIX  Foundation and Permission Limitation. 

Point # 10 - Disk Cleaners, Optimizers and UnInstaller are not needed. They will often times attempt to Modify, Alter, Remove or Delete elements of the Operating System requiring a Re-Installation.

Point # 11 - Do you have a Rescue Plan In-Place. This comprises having 3 Backups using 2 methods and 1 Off Site incase of Theft, Loss or Natural Disasters. A Time Machine Backup  is very useful and can be used to Revert to Previous Working macOS. 

Point # 12 - For addition purposes - two Tested Bootable Clones each to separate external drives. This is insurance incase the upgrades goes sideways. At least one Tested Clone and / or Time Machine Backup should be Off - Site

Point # 13 - Are the installed Applications / Extensions compatible with Monterey. Check with the Developer for compatible Apps / extensions. Do they offer updates or upgrades. Same goes for Third Party Drivers for Printer, Scanners etc.

Point # 14 - If upgrading from Mojave and earlier versions of macOS - Remember that Monterey does not support anything 32 bit. These include Applications, Extensions and Drivers for any devices. There is no workaround.

Point # 15 - To check for 32 bit Applications - a good application to use is Go64 - safe to use.

Some users have had problems skipping Big Sur and even fully updating Big Sur before upgrading to Monterey. As Dialabrain siad, what exactly happened when you tired?

One thing you do need is an Apple Disk installed internally since part of the upgrade includes update the Mac's firmware and that requires writing to an Apple disk so the firmware can be updated. If no Apple disk the upgrade to Monterey fails..

I'd recommend to have a real backup first!

I did the exact same upgrade on a MacBook Pro (2019) and I ended up with a system that would not boot. It complained about not being able to migrate user files, but all files were actually present. Luckily I did have both time machine (no, restore from time machine did not work either) and an external mirror disk.

In the end I reinstalled Monterey fresh and used the mirror as the source of files. After that I copied the remaining Apps from my TimeMachine backup. That worked like a charm. I have heard of people, who upgraded successfully, but for me it was a real problem, especially on my main work machine.

Much luck!

DeniseRene wrote:

Why can't I upgrade from Catalina to Monterey?

Assuming your iMac is compatible you don't need to upgrade to Big Sur first.

What happened when you tried?