What are some of your deepest space man regrets/mistakes?

[Technature]

Sometimes I still forget to search people properly after arresting them.

And not the "That's totally a normal pen" thing (which I tend to do on purpose because it feels dickish to take something that's supposed to seem harmless).

I mean the "Oh yeah you can keep that utility belt, no problem...wait, why is there a hole in the brig now?"