Scholarship on prison masculinities to date has primarily centered on the most revered, dominant, or hegemonic forms, with little attention to how subordinated prisoners negotiate masculinities at the bottom of prisoner hierarchies. This article, drawing from a wider qualitative study on “revolving door” imprisonment, charts the shift from normative to subordinate masculinity for a group of men housed in a segregated Vulnerable Prisoner Unit (VPU) in an English prison. I show how these men, influenced by their previous prison status and criminal history, adopted different—more costly and high-risk—situationally adaptive strategies in negotiating their masculinities at the bottom of prison hierarchies. Exploring their subordinated prison identities reveals the dynamic, relational, fragile, and spatial elements of their masculinities. I conclude by suggesting that a greater focus on subordinated carceral masculinities adds a much-needed divergence from the preoccupation with hegemonic or dominant prison masculinities. This divergence offers researchers a new opportunity to shape and to inform policy debates on how, in extreme environments like the prison, alternative ways of “being a man” might be opened up to those who have suffered at the most brutal end of prison hierarchies.