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Jack's Swear Jar, also known as the CaF Swear Jar, is a segment of the podcast covered after the intro. It began in Episode 4 as an attempt to rein in the overwhelming number of F-bombs uttered by Josh. In Cthulhu & Friends, there is a 5% chance of death if a character happens to roll a critical failure. Every ten F-bombs uttered adds an additional 10% to this "I'ma Die" die.

As of Episode 11, the punishment has officially been expanded to include the entire cast. A d6 rolled by Veronica determines who will receive the punishment. In Episode 17, Veronica dropped more F-bombs than all the players, so she granted them all a bonus: a re-roll of any one Sanity check or critical failure.