Context: My players had just washed up on the shores of an island inhabited by a strange cult, who were there to capture them as they arrived. The party killed the cultists, and took their leader to interrogate. The knight (Battlemaster fighter) decided to helm the interrogation attempt.
Fighter: Who are you working for?
DM: Roll intimidation
Fighter: *Rolls Nat 5*
DM: The cultist leader spits in your face and laughs, saying he will tell you nothing.
Fighter: I cut off a finger.
DM: Roll intimidation with advantage.
Fighter: Nat 4 and Nat 3.
DM: The man screams, but eventually grits his teeth and tells you nothing.
Fighter: I cut off another finger.
DM: You can’t chop off all of his limbs until you get a good check.
Fighter: Technically they’re appendages. Can I cut off his hand?
DM: I wouldn’t give you another roll for it.
Fighter: We’re on the ocean right?
DM: Yes?
Fighter: I’d like to waterboard him with his own robes.
DM: Jesus. Alright, roll intimidation for waterboarding.
Fighter: Rolls Nat 1.
DM: So this poor man’s hands get loose from about the ten minutes of waterboarding, and he stabs himself with a dagger to end the pain, so you can’t find new ways to fail intimidation checks.
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