What software you consider so bad it made you happy when you left your job?
I've worked with some pretty rotten software, but management software is easily the most user unfriendly, so my vote goes to HPSM.
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Windows.
I did an internship where my main system was Linux, but it was in a VM on one monitor with the windows host on another for using Windows apps.
I work in IT and my first few jobs were working with Windows doing Desktop Support. It was extremely boring and annoying. I've been a long time Linux user and broke into that side, professionally as soon as I could.
Came to comment Windows as well.