The statutory retirement age in Nigeria is 60 years or 35 years of unbroken active service, whichever comes first. After retirement, civil servants are entitled to benefits such as gratuity and pension. However, for decades, State governments in the country have had challenges paying retirees’ gratuities and pensions. These challenges have made retirement from civil service dreadful to intending retirees. Consequently, the federal government of Nigeria adopted the contributory pension scheme in 2004 to replace the defined benefit pension scheme that was operational. The scheme was amended for better efficiency in 2014. Nevertheless, most States in the country are yet to adopt the new scheme. Kwara State is included in the list; the State still operates the defined benefit scheme. In recent years, there have been reports of retired civil servants’ protests over none payment of pension in the State. To this end, this paper examined the socio-economic and transitional experiences of retired civil servants in Kwara State. Qualitative methods of investigation were utilized. Snowball and purposive sampling methods were utilized to access participants. In-depth interviews were conducted on 18 retired civil servants in the State. Interviews continued until the point of saturation was achieved; then, no new knowledge was forthcoming from subsequent interviews. That point was achieved on the 16th participants, but interview went on to the 18th participants for validity sake. This was supplemented with six gender based focus group discussion (FGD) sessions. Six participants constituted each FGD session. The interviews lasted between 48 and 65 minutes, while FGD lasted 90 and 120 minutes. For the purpose of internal validity, three staff of Kwara State Pension Board were interviewed. Constant comparative analysis of grounded theory was employed for the purpose of analysis. As per this method, utilizing open, axial, and selective coding, the data were gone through line by line to identify concepts and categories and the core categories respectively. The transitional and post-retirement experiences of the retirees, the reasons for these experiences, their coping strategies and recommended solutions were identified. The outcome of the study showed that retired civil servants: (1) were intermittently and rigorous screened; (2) were owed gratuity for several years; (3) local government retirees’ pension were paid in percentages throughout the year 2016; (4) modified their lifestyles and took up other income generating activities; and (5) post-retired years are characterized by health and acute financial challenges. Retired civil servants in the State called for old age policies that will eradicate sudden deaths that presently characterized their post-retired years as a result of poverty and unattended health challenges.