This study investigates the impact of digitalization and Artificial Intelligence (AI) on prison administration, criminal records, and offenders' re-entry, particularly on elderly convicts. International research in countries like Australia, Japan, Sweden, Canada, France, and the UK highlights the increasing challenges posed by ageing prison populations. The study, conducted in central prisons in Tamil Nadu, India, employed a descriptive research design and purposive sampling method, involving 259 participants across five central jails. Utilizing qualitative and quantitative analysis methods, including SPSS software, the study identifies post-release challenges faced by elderly inmates in society and the workplace, emphasizing issues of diversity, equity, inclusion, and social justice. It concludes with insights into the coping strategies adopted by older offenders to navigate these challenges, underscoring the need for societal understanding and support for their successful reintegration.