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The Elder Scrolls V: Skyrim Hints
Speak to Sibbi Black-Briar.
1 of 4: Approach the entrance to Mistveil Keep, then look to the right of it for the entrance to the Riften Jail area.
2 of 4: To get past the locked door in the jail, talk to the seated guard and bribe him or pass a persuade check, or quicksave and try pickpocketing his jail key until you succeed.
3 of 4: Past the door, go straight down to the wooden railing, then go left to find Sibbi Black-Briar's cell.
4 of 4: Talk to him about Letrush sending you, then try to pass the persuade dialogue option that comes up. You don't have to, but it'll get you an optional objective and the key to a strong box.
