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The Elder Scrolls V: Skyrim Hints
Locate Brynjolf at the Ragged Flagon.
1 of 8: Go south from the inn and cross a curvy wooden bridge, then turn right and go down some stairs.
2 of 8: Cross a small wooden bridge, then turn left to reach the door that leads to the Ratway area.
3 of 8: Sneak down the first passage and try to get the drop on the two hostile fighters ahead, then continue to where you reach a drop-off.
4 of 8: Turn left past it to find a locked door. If you can pick it open, you can shortcut your way to the room where a lowlife attacks you.
5 of 8: Kill the lowlife, then check his table for a Pickpocket skill book.
6 of 8: TIP: Go through the doorway near the room's NW corner and use the lever on the right wall to lower a bridge. That'll create a shortcut back to the exit.
7 of 8: Look on the east side of the lowlife's room for a door that leads to the Ragged Flagon.
8 of 8: Get up on the floor next to the bar and talk to Brynjolf to get the next three objectives. To also get the three optional objectives, ask him about each of the people you're collecting from.