The “pains of imprisonment” is one of the most prominent concepts in the social study of incarceration. First introduced by Gresham Sykes in 1958, it has subsequently been taken up by generations of authors and applied to an increasingly diverse range of contexts, populations, and activities. This article details how the “pains of imprisonment” concept has evolved and expanded. It is based on an analysis of 50 academic works (books, articles, and chapters) that used some variation of the “pains of…” formulation. We identified four main trajectories in the literature that have contributed to this expansion, which we document in the first section through the use of illustrative examples. This is followed by a more critical series of reflections that seek to appreciate some of the organizational and political factors that might account for the appeal of this concept. Finally, we conclude by questioning whether the “pains” framing might paradoxically be a victim of its own success, with its analytical and political purchase potentially blunted through overuse and overextension.