Upgrading to Monterrey from Catalina

I’m still running Catalina, and thinking of upgrading to Monterrey. (I try not to install the latest greatest OS on my Macs, so I would do this before Ventura comes out.)

The question: What am I risking if I do this? I rely on a fair bit of coding and automation software including:

  • Keyboard Maestro
  • Hammerspoon
  • Python 3.x via Anaconda
  • Bunch
  • PopClip
  • Karabiner-Elements
  • Hazel
  • Drafts
  • TextExpander

Other essential software:

  • BackBlaze
  • 1Password (7 atm, but expect to upgrade to 8 eventually)
  • Dropbox (sigh)

Any/all warnings, tips, concerns, etc. are welcome. Thanks!

In my experience, macOS Monterey has been flawless. I would definitely update, especially with support for macOS Catalina ending in the coming months.

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At this point everything that is regularly updated is good for Monterey. The software I use all works fine (some overlap with your list). I don’t love Monterey, there has been a trend in macOS to hide info and remove options that I really dislike, but that is only going to get worse. Might as well update now if you don’t want to get forced into October’s(?) macOS release.

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I use the above with no problems on Monterey.

I think there’s been discussion of “Dropbox is finally compatible with Monterey” elsewhere here on the forum. I’ve switched to Box myself.

If you want to wait on Monterey past October, go ahead and download the installer, but don’t run it. You can hold onto it as long as you like. There may be other ways of getting old versions, but this is how I keep a backlog of old installers, just in case.


How’s it working? When I first moved to the cloud, I started with Box … it was fine*, except then I discovered that (at that time) it didn’t handle Mac-style bundles – directories that looked like files. I lost some data, discovered that Dropbox handled them beautifully, and switched on the spot.

I’ve always assumed that Box would eventually handle bundles fine, but haven’t risked finding out.

  • not sure I could ever describe any cloud sync service as much better than “fine”…