The University for the Third Age, a relatively new concept in Lebanon, provides educational and social opportunities for older adults. The goal of later-life educational institutions supposedly covers more than a mere provision of learning. This being said, highlighting the significance of rewards associated with older adult learning--and the barriers it faces--is needed. Through this study, we hope to deepen the understanding of the benefits of later-life learning. In addition, we also pay special attention to environmental and social factors that were previously excluded dimensions of the challenges to learning. We explored the benefits perceived by older adults after finishing one term at a University for the Third Age in Lebanon. Also, we distinguished between the different types of barriers faced by seniors in the same context. We included 461 older adults from two cohorts, and we followed a qualitative approach, using content analysis of 247 solicited answers to our research questions. The data consisted of relatively short answers describing self-perceived benefits of the learning experience, as well as its perceived challenges. Findings indicated the existence of three types of benefits: social, cognitive, and psychological, with cognitive benefits the most reported ones. In addition, educational challenges were categorized into dispositional, situational, and institutional, with the latter being the most reported. After interpreting the findings with the Self-Determination Theory in mind, it was concluded that educational challenges negatively affect the well-being of older adults, while educational rewards could enhance it.