Sly, Murray, Sir Galleth Cooper, and Carmelita Fox entered the castle and confronted the traitorous Penelope, who then enters a giant armored suit. As Sir Galleth charged at Penelope in an attempt to stop her, she grabbed his cane and trapped the gang between the drawbridge's gates. Before they slammed shut, Carmelita pushed Sly out.
The battle then starts and Penelope begins attacking Sly by firing missiles at him, causing the ground to ripple. Sly dodges the ripples by jumping onto the wooden towers throughout the arena. He uses his Archer Costume to fire bombs at the giant robot and remove the armor. After disabling the suit, a piece of the armor falls on Sly's leg and pins him. Penelope takes this moment to try to kill Sly, but Bentley appears in Penelope's a suit made of the Moat Monster.
A heartbroken Bentley asks why Penelope turned on the Cooper Gang. She explains that it was because of Sly's morals and that they were holding back Bentley's potential, which he could have used to make them rich. Bentley tries to reason with Penelope, to which she insists that they fight as Bentley decides to stay loyal to Sly.
The two fight, and after the brawl, which Bentley won, he freed Sly from the fallen armor, and he apologizes for not helping the gang when they needed it. He then opened the gate to free the others and the mission ends.
- Murray is seen swimming in this level in his Ultimate Murray scuba suit, despite not being able to swim in gameplay, even while wearing the Ultimate Murray suit.
- This is the first time Bentley's playable since being disabled in "Shell Shocked Heart."
- This is the only boss fight where two characters fight one boss in Sly Cooper: Thieves in Time.
- When fighting Penelope, one of Bentley's comments is that her "mech design is so 2005," a reference to Penelope's debut in Sly 3: Honor Among Thieves, which was released in 2005.
- For the first time, the setup for an operation isn't made by Bentley, but by Carmelita.
- This is the only heist in the game to feature a job completion screen, similarly to how most heists in Sly 2: Band of Thieves and Sly 3: Honor Among Thieves did.