With Sly in jail, Bentley went out for reconnaissance to find a way to break him out. He took three pictures of the prison where Sly was being held:
Prison tower – The location where Sly was taken after his arrest
Arsenal – A pile of TNT located on one side of the prison
Rear wall – A boarded-up hole on the rear wall of the prison
At the prison, Sly was escorted to his cell. Upon arriving, he greeted "Tennessee Kid" Cooper. Tennessee was surprised to see somebody else in his cell, and assumed that he must have made Toothpick quite angry to have been thrown in there. When he asked his new cellmate his name, Sly responded. Tennessee was angry at Sly as he believed Sly was "funnin'" on his family name by claiming he was a Cooper. Sly swore that he was not joking about his name, but Tennessee said that he would only believe him if he broke them out of their cell.
Just then, Bentley radioed Sly and told him that the large iron ball attached to his Jailbird Costume would be able to break the prison cell's walls with ease. Sly tried it out, and created a giant hole in the tower, which he escaped through. He then used the ball to break down the cell's door for Tennessee to escape. Sly utilized the costume to move various cell blocks to create paths. Afterwards, he and Tennessee came to the arsenal of TNT Bentley had photographed during his reconnaissance. Per the turtle's orders, Tennessee carried a barrel of the explosive while Sly continued making a path through the prison. After making their way through flames and floor lasers, the duo reached the rear wall of the prison. Tennessee placed the TNT barrel next to the boarded-up hole and lit the fuse. Once it exploded and created an exit, the two Coopers escaped via Sly's paraglider.