So I did that quest you pick up in Whiterun where you have to free a high-profile prisoner from imprisonment. I find the dude hanging off a wall in chains, tortured half to death. I get him off the wall, and I think to help him get out of here and get back to safety, I'd better give him some gear. So I reverse pickpocket a sword and some armour on to him. Well he detects it, "25 bounty added", and he starts pummeling me with his fists. [censored] arsehole. I shot him to pieces and failed the quest.

I wonder why reverse-pickpocketing has a chance for failure, if you're giving someone something. If I was to give a beggar 300,000 gold, they shouldn't turn hostile if caught.

But, you could also be giving him poison...

Yeah, he confused sword + briastplate for poison.