Long-standing commentaries about men's reticence for accessing clinical medical services, along with the more recent recognition of men's health inequities, has driven work in community-based men's health promotion. Indeed, the 2000s have seen rapid growth in community-based programs targeting men, and across this expanse of innovative work, experiential and empirical insights afford some important lessons learnt, and caveats to guide existing and future efforts. The current article offers eight lessons learnt regarding the design, content, recruitment, delivery, evaluation and scaling of community-based men's health promotion programs. Design lessons include the need to address social determinants of health and men's health inequities, build activity-based programming, garner men's permission and affirmation to shift masculine norms, and integrate content to advance men's health literacy. Also detailed are lessons learnt about men-friendly spaces, recruitment and retention strategies, the need to incrementally execute program evaluations, and the limits for program sustainability and scaling. Drawing from diverse community-based programs to illustrate the lessons learnt, caveats are also detailed to contextualize and caution some aspects of the lessons that are shared. The express aim of discussing lessons learnt and their caveats, reflected in the purpose of the current article, is to guide existing and future work in the ever growing field of community-based men's health promotion.