First time I came across Torach Tor Spices, I thought they were spices like curry, cumin or turmeric powder. Anyway a few systems later, I got interdicted and attacked by a pirate. Then the local security services turned up, I thought it is OK the security services are here they'll help me take care of the pirate. They scanned me, declared I was carrying contraband goods, and proceeded to attack me. I consider this to be a Homer Simpson "Doh!" moment.
When I first bought E.D. I had my first docking moment with my Sidewinder. I wanted to get it right so I meticulously spend ages reading it up and watching You-Tube videos about it. Anyhow when it came to that first time, I couldn't for the life of me dock the bloody thing. There were no error messages or warnings, I tried slamming it down, but no, still nothing. At some point my docking period expired I was then a trespasser and the station started firing at me. Slam, slam, slam, nope, not happening. Boom, and I rage quit. It took me a while to work out what I had done wrong, I believe my pitch was at unacceptable angle for landing, but to be fair there were no error messages or warning signals of any kind.
How about going to do some bounty hunting as part of a CG in a wing. I turned up at the HAZ RES, in my Conda, in a hurry because my wing mates were waiting for me. Seconds later every pirate and his dog is attacking me, what the hell! Well the other CG in the same system was a trade CG requiring Tantulum to be delivered to the target station, I forgot that I had a cargo hold full of Tantalum (350+ tonnes) for this other CG and I had just come from the target station to get to the HAZ RES for the BH CG, "Doh!".
Another time I was in a CZ with some wing mates in a Python. Found a cutter, targeted him and said "Right, your gonna get it now". I let him have it with my BIG gun (a fixed beam class 3 laser) only for ice to form on the screen of my space ship. - My secondary weapon was set to my heat sink instead of my fixed beam class 3 laser, "Doh!". The worst thing about it is it took me a fair bit of head scratching to work it out.
You know when you are docked below in a station docking port, their are 3 options on the main menu in front of you, "Starport Services", "Goto surface", "Launch", or something like that, in that order. Well one time I thought I'd just pop off and get a cup of tea, but to save me a tiny bit of time I'll send my ship to the surface so I am all ready when I come back to launch and go. "Doh", I came back to a screenful of smoke and flashes and then just before I realized what was happening up popped the insurance screen for a fully A-Rated Python. I had selected "Launch" instead of "Go to Surface" just before I left to get my cup of tea.