Transmasculine (i.e., female-to-male transgender) individuals have lower rates of cervical cancer screening than nontransgender women and often report negative experiences with the Pap test. Deciding to undergo screening and the test experience itself are characterized by the following processes: negotiating identity as the patient, provider, and insurance company wrestle with the degree of (in)congruence between a patient’s masculine gender identity and their conception of the Pap test as feminine; bargaining for health as a Pap test may be required to obtain medical transition services or avoid undesired health outcomes; withstanding acute challenges during the Pap test to body, identity, and privacy; or reframing challenges as affirmation. The degree of distress triggered by the Pap test varied from “routine” to traumatic. Participants affirmed that a trusted, trans-competent health care provider could significantly reduce barriers to regular and satisfactory cervical cancer screening. Data are from 32 in-depth interviews conducted in Boston, Massachusetts, with transmasculine individuals; a modified grounded theory approach informed the analysis.