Because of TCC/PPPC, which Apple introduced in macOS 10.14, scripts and applications have to ask for permissions to do certain things, especially things like reading user home directory files.

If you have an Outset login script that tries to access something in the home directory, you may find in the ~/Library/Logs/outset.log that you get a Failure processing [name of script, command that failed] Operation not permitted error.

I tried creating a PPPC profile for the script itself. That didn’t work. I tried creating a PPPC profile for /usr/local/outset/outset. That didn’t work. I tried creating a PPPC profile for /bin/zsh. That didn’t work. I tried creating a PPPC profile that allowed all three to have access to all files. That didn’t work.

So, finally, I ran a tccutil reset All to reset the database, and then I logged in again, and it asked for Python to have access to the home folder the script was trying to read.

So I created a PPPC profile to allow Python (the one Outset is using) to have access to the home folder the script was trying to read, and the script ran just fine.

I’m not an expert on this, and any follow-up questions you have would probably be best directed to the #outset channel on the MacAdmins Slack (I’m over there too) instead of in the comments of this post (blog comments aren’t a great venue for tech support), but I thought sharing one case that worked might be helpful for others running into the same issue.