Remote OS Upgrades

@ChrisTech Unless you're going to have the user initiate the install by running the Install macOS Catalina app themselves you really don't want to be using the App Store stub installer. You'd be better off using the macOSUpgrade workflow.

We've used that in the past, but I guess the issue is now people are working from home and we will need to setup an external file distribution point for ~1200 machines to download an 8GB file, 1200 times. Normally they would be at their site where I have caching servers to do the heavy lifting.

@ChrisTech One alternative you might try is that instead the policy that macOSUpgrade calls to download the installer doing that download from your DP, you could adopt the erase-install script to download the installer directly from Apple's servers. I've used that trick in the past, but you have to be aware that when Apple releases an update to macOS the old installer is normally removed from their servers at the same time.

Whoa thanks @sdagley I am putting together something now that uses the installmacos.py script. Gamechanger. Wish I had known about it. Thanks for pointing me in the right direction.

@ChrisTech You might find erase-install (ignore the name) a better starting point as its core is installinstallmacos.py, but it has the option to download the macOS installer and copy it into /Applications.

After looking at it, that's what I did. I had to make a custom installinstallmacos.py to work on 10.12 and host it somewhere else. I was able to build a Self Service policy with the scripts and successfully upgraded a machine from home!

Take a look in this thread is you haven't. Ther's a LOT of info here you can use to build your next upgrade policy. Also, https://www.jamf.com/blog/reinstall-a-clean-macos-with-one-button/