Most research on prison life is concentrated on younger generations yet older prisoners are increasing in number in our provincial jails. This phenomenological investigation aimed to explore the lived experiences of older inmates and how they cope with aging behind bars. A purposive sample of elder offenders who are 50 years old and above and have been incarcerated for more than two years was utilized in this study. Data from in-depth, semi-structured interviews of nine key informants were analyzed using the Colaizzi’s technique. Three major themes emerged:(1) issues surrounding self; (2) threats to physiological integrity and (3) social structures. Despite being deprived of liberty, older prisoners’ feelings towards their families remain the same. Sub themes such as the acceptance of their aging bodies, their fear of rejection, the sense of being a burden, self-pity as a consequence of envy and fear of dying in prison add to their psychological struggles. Although still yearning for freedom, being productive is perceived as a vital requirement for reentering society. Spirituality was a means to cope. Restrictions in daily activities, environmental barriers, needs for intimacy, and their predispositions to diseases were considered as threats to their physiological integrity. The dilemma of role preservation versus discontinuance, convenience versus discomfort, and the critical role of discipline reflected how the social structures within the prison system affect the lives of older inmates. The current socioeconomic patterns within the penitentiary still regarded the older “mayor†as a source of wisdom. Findings suggest that the phenomenon of aging behind bars is multidimensional with two major goals: freedom or “laya†and survival or “sugakod.†The family is the central concept in between and acts as the motivating force to attain freedom and survival. A holistic approach is recommended to improve the social conditions within the prison system.