Gintoki's plan to stop an evil warden causes a riot.
With tension brewing between some of the inmates and the guards, Gintoki and his new underling Shachi make their way to the warden’s office to get something on the warden, using the chaos that a stolen set of keys results in to sneak in.
All they need now are disguises, however Gintoki chose the wrong time to steal a uniform from one of the guards, ending up with his pajamas instead. and while the sight of a guy running around in his pajamas, conveniently designed to still look like a prison uniform, would be enough to arrouse suspicion, he simply believes that the guards will see him as a guard in his pajamas, and if not a pajama kid. Surprisingly, this ploy actually works and they’re able to get past. However while they were doing this, the other prisoners seize control of the prison.
Having made it to the warden’s office Gintoki and Shachi stumble upon a surprising truth, that the old man’s son had died some ten years earlier yet his letters are still replied to, meaning that the warden has been responding to them all along. That all the measures that he took to keep the old man inside were in order to keep up this illusion, and as the riot goes on Gintoki resolves to make him pay for lying to the old man. With Shachi returning to his old self to buy him some time. Elsewhere in the prison the warden had managed to break free and group together with some of the guards and other prisoners, stepping up when it looked as if the old man was about to get hurt. And knowing that the rioters are after him alone, he gives them one last letter and attempts to buy some time, with this letter confessing the truth that his son just has difficulty responding, expressing his gratitude to him for helping him when he first got this job. But just when it looked as if the rioters were about to do away with him, Gintoki comes to his rescue and intends to keep him to the promise that was made about his release.
In the end the warden takes responsibility for the riot and commits seppuku, feeling that it was his fault for treating the prisoners as toys, but still Gintoki intends to make him pay for one more thing, donning his cap and leading him along a line of prisoners in guard uniforms to the visiting room. Where he meets none other than the old man who wishes him the best of luck and tells him that he liked his last letter. That he had still been writing to his son all along, and asks him if they can still make small talk like they’re always done. And as Gintoki steps out the gate he catches a pudding cup flung over the wall.
- Shinpachi and Kagura appear in Gin's flashback but have no lines.