Despite having just defeated the Devil, the guilt from his sin is still plaguing Cuphead's mind. There's one more question over the matter that he's dying to have answered, but can he break his true feelings to Mugman before the feelings break him first?

A year or so after defeating the Devil, Cuphead and Mugman face their greatest challenge yet: coping with the death of Elder Kettle.

Wander is infected with a serious illness called Blumonia, and must remain quarantined in the hospital until he recovers. Sylvia offers to do good deeds for him during his absence, but, even in his sorry state, Wander wants desperately to go help others outside. Can he keep his impulses under control for his own safety?

The Warden has reached a breaking point. He can no longer control the chaos, or mask his inner turmoils with rainbows and prisoners' blood. He wishes fill his lifelong emotional void, and finally obtain true peace of mind. His father's ghost returns to reclaim his place as the prison and family mogul, but one other soul will stop at nothing to save the Warden once and for all.

In honor of their recent heroic deeds, the President invites Flint and the gang to speak at the White House, and make plans to expand Sparkswood across the globe. During their stay, however, Flint is diagnosed with Asperger Syndrome, and he creates an invention to try to get rid of it. But on Halloween night, the device goes awry, and deforms Flint's brain into that of a monster!