Often times when I try and free random prisoners from the Justicar, one or more of three things happens:

1. I accidentally hit the prisoner and he attacks me or

2. If I kill his Justicar guards, and he is free, that means there is a witness to a crime and I get a bounty. On the other hand, if I kill the prisoner there is no witness. Really? This is so stupid.

3. I keep trying to give the prisoner weapons and stuff which is an option (if you can catch the prisoner when he runs from you?!) and the weapons disappear from my inventory but don't seem to appear on him.

Arg.

Why would you free the prisoner? He's a Stormcloak traitor.

First off, love your avatar. I'm watching SoA right now and would totally join a Tatooine charter, just not if Anakin is the President.

But the only thing I really agree with is number 3. I did that expecting him to pull out the stuff I gave him to help me kill his captors. But nope, he went charging in with only his fists.

For number one I say it makes sense, as I would defend myself if attacked. But it might make more sense for him to flee and the guards to attack, as he is basically defenseless. Also, why does the first attack you hit him with cause the bindings on his hands to unravel?

For 2, I agree it is screwed up a bit but that doesn't happen if you free him first as they become hostile to you. Not exactly useful for an Assassin though.