Remain Undetected - 225 G
No Kills or Knockouts - 115 G
1 Aerial Takedown - 70 G
Lift All Loot Items - 290 G
You Must complete Chapter 4: A Friend in Need to unlock this client job from Vittori.
Objective 1: Steal the Octopuss
It should be noted that it is impossible to complete all four Thieving Challenges in on play through. For this reason, we will show you how to finish three of them, leaving No Kills or Knockouts for you to do a second time through.
When the job begins, head upstairs and look outside to see an anchor beam. Put a Rope Arrow into it so you can easily get inside the house. Below you is a single guard. He's far enough away that you can't perform an aerial takedown, so either put a Broadhead Arrow in his skull or simply leave him be, leaping to the rope.
As soon as you're inside, loot the room and then go through the door into the bedroom. Loot this room but be careful that the servant doesn't spot you as he talks to the collector. When the servant goes to move, you have two options: swoop behind and knock him out, or let him go. Either way, loot the place and climb out the east window when you're done.
Grab the poppy from the ledge before dropping down into the alley. You can pickpocket the guard and loot the nearby area. If you aren't going for the No Kills or Knockouts Thieving Challenge, you can take out both of these guards. Whatever you choose, when you're done, climb back up and through the window you just exited.
If you're taking the pacifist approach, the servant is alive and went outside to talk to the guards you just encountered. Head downstairs and loot the area with the two tables. Be careful opening the east door, there's a guard inside. Wait until he calms down and then knock out the lights in the room with a Blunt Arrow. He won't bother to turn them back on. Sneak into the room and start looting. He stands in the way of some loot, so try throwing a bottle back into the room you were just in, causing him to check out the disturbance. Pick his pocket as he walks away, then grab the candlestick and use the Razor Tool to snatch The Court of Montonessi (9/12) - What Is There Cannot Be Seen. You have to be quick, the guard will head back to his original post.
Continue looting this floor, being careful to avoid the guard. If you come across any light switches, hit them with a Blunt Arrow to help keep yourself concealed. Of course, if you decided to kill or knock the guard out, ignore the sneaking tips and loot the place. There's only one more guard to worry about if you're taking the violent approach. He's located in the cellar.
When you've collected all the loot you're after, head back upstairs and climb back out the east window, just as you did before. Hit both the torches on the east wall with Water Arrows, then drop behind the guard and pick his pockets. Sneak past the guard, climbing the nearby crates and making your way counterclockwise around the yard to the cellar stairs. If you're looking for one Aerial Takedown, this is a good place to get it. Keep in mind there are two guards here, so try using a distraction to separate them and Remain Undetected.
Be careful of the guard in the cellar if you plan to leave him safe and sound. Otherwise, take him out in whatever way you want and begin looting. We'll walk you through how to leave him alive since killing him would mean you only have the looting left to do.
Sneak down when the guard isn't looking and hit the lights in the cellar. He's going to turn them back on, but you can loot the area quickly before he's done. When the guard resumes his patrol, look for the two switches on the west wall's painting. If the guard is alive, you might have to try this several times as he makes his rounds. Continue to turn out the lights and use distractions to buy you the time you need. The same goes for entering the combination. If the guard remains on patrol, you might have to enter the combination one number at a time, swooping back to the shadows to avoid detection. The combination to the safe is 8-1-2.
A wall panel will move away, revealing a hidden doorway. Enter when the guard isn't looking, being sure to close the door behind you to avoid suspicion. Once you're safely inside, plunder everything, including Client Loot (7/8) - Octopuss.
Objective 2: Escape the Collector's Lodge
Use your Focus to identify a loose brick in the wall. Press the brick to gain access to a secret room. Head down and loot the place, grabbing Whiteridge's Duty (4/6) - The Virtuous Lady. With that, you should be carrying all three of the jobs Collectible Loot Items.
It's time to make your escape. If you've killed or knocked everyone out, consider skipping and whistling as you leave. If everyone is still alive, stick to the shadows, backtracking all the way through the lodge, back upstairs and out through the bathroom window where you started the job. Jump to your rope and then to the ledge to finish things.