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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]
Go behind Skull Keep and bomb the supports of the bridges to make a stairway to the top
Fight the guards
Use the new Grapple-Cam to lead Penelope to the safehouse. Hint: You can't blow up the Grapple-Cam, otherwise, you fail the job.
The job will start with Bentley standing ready with the Hover-Spectrometer. He will launch it, only to Bentley's and Penelope's horror, a guard will shoot it down, scattering the pieces. After a bit of talking, Penelope tells Bentley that her gear is designed to self-destruct if anyone tries to pick it up after a malfunction. After some pondering, Penelope remembers that her RC Car has the same code base as the Hover-Spectrometer, meaning that the RC Car can read the data of the pieces. After all seven pieces are analized by the RC Car, Penelope will bring the RC Car in, and Bentley will read the data. He says that there is a chest that was located. Control will switch to Bentley. Make your way to Skull Keep's drawbridge. LeFwee noticed the disc, and raised all of the drawbridges. Bentley tells Penelope that he's dealt with guys like this before. They can't trust their own men, so they keep an escape route handy. It's located near the anchor that was dropped on Stone Jake's head. Cross it and reach the back entrance. It's locked, so bomb the upper stair's supports to make a walkway up to the top. Once on top, LeFwee will have a conversation with a pirate, kill him, and bring out Second Mate Jones. He will promote him to captain of the guard, and then leave to torture the prisoners. Once he's gone, attack the pirates! Once they're all defeated, Penelope and Bentley will have to do a double-button door. Once inside, Bentley and Penelope will examine the chest. Bentley says it's thick with traps, although Penelope says it has none. To be safe, Bentley runs back to the safehouse to get Penelope's spanners. Penelope goes against Bentley's advice, opening the chest. Sadly, it's rigged with blinding mist sprayers that get Penelope. She falls down in front of the front door to Skull Keep. Bentley comes up with a plan to take a turret off of her RC Car and attach it to his Grapple-Cam. You then have to use the Grapple-Cam to destroy the bridge's supports, and lead Penelope back to the safehouse with the bird noises of the Grapple-Cam. Once Penelope is back with Bentley, he'll take her in to make sure that the dust has no permanent effects. After that, it's job complete.