For some reason whenever I'm on my work's VPN, Apple Music lets me play 1 album and then the next time I try to start a song it will tell me I'm not logged in and I'll have to force quit and relaunch (frequently a few times) before it will let me play another album.

Apple Music is the only app that has this problem.

Apple uses certificate pinning for some of its domains, which doesn't play nicely with corporate firewalls.

https://support.apple.com/en-us/HT210060

Either a company block traffic or allows it.

Inconspicuously inspecting traffic to spy on people, even employees, is just bad.

I work at a company that once turned it on for GitHub.com.

All builds that pulled stuff from GitHub started to fail because all those Docker containers don't have the company's root CA trusted.

I was thinking of Jira

ServiceNow, for me.

Gotta be SharePoint.