This Con­tri­bu­tion exam­ines whether com­pli­ance with the Fifth Amend­ment should shield a fed­er­al con­dem­na­tion action from a First Amend­ment retal­i­a­tion claim. Han­nah Beat­tie (’21) argues that the ratio­nales for carv­ing out safe har­bors for gov­ern­ment action to be free from First Amend­ment scruti­ny if in com­pli­ance with the Fourth Amend­ment do not extend to the Fifth Amend­ment con­text. Ulti­mate­ly, this Con­tri­bu­tion con­cludes that an indi­vid­ual should be able to raise a First Amend­ment retal­i­a­tion defense to a con­dem­na­tion action, even if the gov­ern­ment com­plied with the Fifth Amendment.