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Fathers play a significant role in shaping family life. Yet Australian men’s transitions to fatherhood have been neglected in research and in antenatal support/education programs. Drawing on contemporary theories of masculinity, this article explores how a cohort of 25 first-time fathers in Tasmania, Australia, experienced 2 different father-only antenatal support/education groups. In particular, I was interested in how men negotiate masculinity and “involved fatherhood” in the context of these groups. I argue that the settings in which Tasmanian men are invited to prepare for fatherhood can be experienced in contradictory ways (e.g., pubs vs. hospitals or community centers). Strategies to better support men in the transition to fatherhood are offered in the concluding discussion.