Penelope: Roger, Bentley. Let's light this candle.
Bentley: Be still my heart!... She made an obscure NASA reference! Why do the girls always have to go for Sly? It's just not fair!
Penelope: What was that? I didn't read ya.
Bentley: Uh... nothing. I was just saying... that we've got... fair winds for lift-off. Let's do it.
― Penelope and Bentley at the start of the job[src]
Penelope has created a Hover-Spectrometer to scan for objects that resemble a safe or chest that might hold the Dagger Island treasure map. They launch it above LeFwee's Skull Keep. A pirate, who is unaware what it is, sees it and shoots it, making it scatter into pieces before the data was downloaded.
Penelope explains how the pieces are rigged to self-destruct when touched. Bentley comes up with the idea to use her RC car to go and collect the pieces. It will be able to download the contents of each piece when collected. Since the pirates are keyed up about spotting the hover disc, they must make sure to stay away from them.
Once all of the pieces are collected, Bentley and Penelope head over to Skull Keep. However, when they get close, they see that the bridges are lifted up and there is no way in. They find a way in through the side, where there are floating boxes in the water. This takes them to the back door, which is locked, but Bentley bombs the supports to a walkway leading up to the roof.
When they get up there, they spot LeFwee along with First Mate Jones. LeFwee comments on seeing the hoverdisk, saying it "just the beginning". First Mate Jones reminds him that its over and everything is fine. LeFwee, who is tired of hearing people's opinions, knocks First Mate Jones off the cliff and sends out Second Mate Jones. He promotes him to Captain of the guards and tells him to double the patrols and keep an eye out. LeFwee heads inside to torture some prisoners.
Bentley must take out all of the guards guarding the door to the treasure. Once done, the two hop down open the double-security door using pirate talk. Once in, Bentley is surprised at seeing so many traps around the treasure, but Penelope claims it will be pretty simple to crack using her spanners. Bentley heads back to the Safehouse to get her tools, while she stays with the treasure to study it some more. However, disaster strikes when she gets the chest open and takes the map, but gets blinded by dust that spurts out of the chest. Unable to see where she is walking, she takes a fall out of the window, landing by the front door. It is up to Bentley to help her get back to the Safehouse quickly and safely. He takes the turret off of her RC car and attaches it to his Grapple-Cam. He uses it to find his way to Penelope and blasts the pulleys to the bridges to let them down. Bentley uses a bird call through the Grapple-Cam's speaker to lure her back to the Safehouse. Once he gets her back safely, Penelope thanks him and he takes her inside to see if the dust has no permanent effects.
- The sound of the Grapple-Cam is often still heard after this mission is complete.
- The turret on the Grapple-Cam is not the same kind seen on Penelope's car.
- It is unknown how the dust was able to penetrate Penelope's glasses.