The scientific agenda that framed the implementation and legitimation of the US invasion of Puerto Rico towards the end of the nineteenth century also enabled the transformation of the occupied territories into laboratories of medical experimentation with human beings. This article proposes the category of "hypochondriac fiction", which names an aesthetic space for the destabilization of biopolitics. This optic is particularly useful for an examination of the work of Pedro Cabiya, since it sets out to undermine regulatory practices (including literary and intellectual discourse), which have controlled bodies and ailments in the island. I first examine the negotiation of alterity in the contexts of economic and biological exploitation as represented in "Relato del piloto que dijo adiós con la malo" (2003) and in the novel Malas hierbas (2009). The manifold syndromes that resolve Cabiya's plot lines as well as the texts included in Historias tremendas (1999) will reveal the ways in which his work disrupts the causal—and etiological—mechanisms at stake in the Puerto Rican colonial laboratory. This essay thus seeks to explain those representational strategies, which replicate the clinical picture designed by intellectuals and medical experimenters while also boycotting, rewriting, and evading such pathological system from within.