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1. kill just the guard(s) that attack. For me, it was just two. (you can revive them later if you want).
2. Talk to Brefft a few cells down.
3. Talk to Hugo and tell him what Brefft told you.
4. Go rest
5. Go back to the jail and a guard will tell you he escaped.
6. Go to the Ancient Battleground north of Checkpoint Rest Town. You will find Hugo and the gang here.
7. You may want to complete every one of Wilhelmina's quests before you do any of this.
Well, I tried your solution. I ended up having to kill all 4 guards inside the gaol. There wasn't a NPC named Brefft anywhere. (I did check the graveyard to make sure he wasn't dead, nothing there) and no event triggered. I can reboot from my inn save but I'm still stuck :/
Well sonof a gun, that did the trick for the guards. Worst. HOA. Ever. There's still no Berfft, But a guard named Dietrich was commenting on Hugo being quiet.
I think I finally got it thanks to you all. The housing permit kept me from getting prison shanked, and resting at the inn after talking to Hugo a bunch made Brefft spawn in his cell the next day. Guess they needed to put out a BOLO for him, thanks agian all!
Good to hear!