This paper examines the lived experiences of selected inmates, some of whom have been released from the New Bilibid Prison in Muntinlupa City, Philippines, focusing on how incarceration has transformed their lives. Confronted with significant mental and emotional challenges, the inmates embraced a new life of faith amid the harsh realities of prison life. The researchers used the phenomenological method to collect narratives from these inmates and employ thematic analysis. The paper identifies underlying themes emerging from these narratives and, in its final section, reflects on them through the theoretical framework of existential philosopher Søren Kierkegaard. Kierkegaard's concepts of the paradoxical nature of despair and the three stages of life—the aesthetic, the ethical, and the religious—provide a lens for understanding the inmates' spiritual transformation through religious participation. By integrating these philosophical insights, the authors deepened the understanding of how prison experiences influence spiritual change. The inmates' journeys from despair to spiritual awakening illuminate the existential dynamics of human freedom, authenticity, and community, as articulated by Kierkegaard. Their narratives provide compelling evidence that even in a setting where freedom is ostensibly curtailed, individuals can achieve a profound sense of liberation by embracing their despair and taking a leap of faith.