Ezra Chitando is one of the most prolific and erudite African scholars of our generation. He has to his credit, well-researched chapters, articles, and books on a wide range of topics in history, religion, and theology. Originally located within the African Traditional Religious Studies domain, the HIV/AIDS pandemic, and his call to serve as Theology Consultant for the Ecumenical HIV/AIDS Initiative in Africa (EHAIA) connived to catapult Ezra into serious reflection on emerging issues and the signs of the times. Africa in general and Southern Africa, in particular, were the epicenter of HIV/AIDS. HIV/AIDS constituted the sign of the time and presented the most formidable challenges to the entire human family as well as the Church in Africa. EHAIA cut a niche for itself by stirring up the Churches through building pastoral and formal theological education competencies for HIV/AIDS responses, amongst other things. It is in this context that “EHAIA series” under the auspices of the World Council of Churches was produced to build HIV/AIDS-competent Churches. That men were also drivers of the pandemic was not a secret anymore. Their participation had become indispensable if HIV/AIDS were to be nipped in the bud. To that end, Ezra Chitando identified masculinities as one area for attention and exploration. This chapter investigates the contribution to scholarship that Ezra Chitando made, particularly in the realm of gender in general and masculinities in particular, their contexts, practical aspects and what came out as Ezra’s signature in his troubling of African masculinities in the many articles, chapters, and books he wrote on the theme.