Years ago, I stumbled across a web based, command line game. It was some kind of infosec/pentesting simulator, I think? But with like... plot. You were doing intrusions, and reading files, and gaining data, and learning about people, and all the puzzles seemed to me at the time to be somewhat technically accurate.
I don't remember where it came from, or any real details about it.
I just remember spending a few hours on it at a stretch for a few months.
This might have been 10 years ago, it might have been 20. It's really hard to say.