We examine dishonest behavior in the face of potential uncertain gains and losses in three pre-studies (N = 150, N = 225, N = 188) and a main study (N = 240). Ample research has shown that people cheat when presented with the opportunity. We use a die-under-cup paradigm, in which participants could dishonestly report a private die roll and thereby increase the odds to obtain a desired outcome. Results showed that the framing of the uncertain situation mattered: Participants who lied to decrease the likelihood to experience a loss used major lies (i.e., reporting a ‘6’), while those who lied to increase the chance to achieve an equivalent gain used more modest lies.