“Some of the moral dilemmas thrust upon us in an age of technique are startlingly unprecedented.” So opens the 1982 essay, “Transsexualism and Christian Marriage” by Oliver O’Donovan, in which he reflects on the new topic of “transsexualism”. Though he wrote the article over 40 years ago, evangelicals today find ourselves still facing transgender identification as novel and startling. This paper will critically revisit O’Donovan’s essay for help. First, the paper will give a tight summary of O’Donovan’s argumentation. Second, the paper will examine what in today’s societal landscape has shifted that may impact how we appropriate his ideas, and also question some of O’Donovan’s moves. Finally, and chiefly, the paper will argue that O’Donovan’s article is more relevant today than ever, and will offer suggestions for how evangelicals can build on his insights in the coming years, to construct a more fully Christian engagement with transgender identities and the values that animate their adoption and support.