The subhuman conditions in Philippine jails and prisons is a pressing concern because of its ill effects in delivery of rehabilitative justice. While many elements are at play, coming from all institutions involved in the justice process, there is a notion that looking into the administrative side of prisons and the role of jail officers oversimplifies the problem and overemphasizes the clout of prison regimes. This study would like to forward an alternative view. Although officers bear authority through their badges, their command over the facility is confronted, challenged, and negotiated by detainees amidst structural deficiencies. Using qualitative methodology and grounded theory, covering data gathered for three and a half years, I discuss officers’ standard routines and techniques in dealing with the order and disorder of jail life. I take the reader toward a custodial venture employed by officers—a route they call “pag-didiskarte” (resourceful strategizing). I conclude with a critical assessment that though “pag-didiskarte” is valued by officers as a permissive relational strategy, it is unsustainable and poses further occupational hazards. I recommend that the country’s jail system can be better managed if officers’ unprioritized, unheard, demonized subjectivities are included in criminal justice development.