Over the years, reports of overcrowding, unsanitary circumstances, and inhumane treatment towards detainees have been increasing. In the Philippines, specific reports on poor inmate living conditions and violence are prominent. Moreover, the incarcerated are placed in life-altering circumstances when the prison cells are overcrowded, resulting in varied prison crowding experiences. This phenomenology study aims to understand how the detainees give meaning to their crowding experiences. Ten (10) male and female Filipino young adult (20–35 years old) detainees from the Legazpi City Jail were interviewed, excluding any participants under solitary confinement or isolation due to precautionary health measures. The participants’ narratives were examined through within- and cross-case analysis, and four (4) themes: Kulong sa kapungawan (longing and yearning), Kulong sa kapanahunan (sentiments over a period of time), Kulong sa pag-asa (experiences that instill hope), and Kulong sa oportunidad (forced opportunities and routine-based life) were rendered via repertory gridding. These contextualized the prison crowding experiences of Filipino detainees specific to family and community concepts in a Bicolano culture. The findings of this research may contribute to intersectionality studies, especially in clinical, rehabilitation, and community psychology. The findings can also be substantial as a springboard for implementing culture-specific programs for the incarcerated.