Second Chance Schools (SCSs) are innovative institutions located worldwide, including Greece, that allow adults who haven’t completed compulsory education to reintegrate into educational systems. This study aims to provide a comprehensive understanding of the benefits and challenges associated with second chance education. Conducted in SCSs within the Central Macedonia region of Greece, the research involved seven school units, with a total of 21 interviews—three from each unit. The study utilised an Interview Guide, and data from semi-structured interviews were analysed using Atlas TI Software. The thematic content analysis resulted in 127 codes grouped into six broader categories. The findings highlight the transformative potential of Second Chance Education on both micro and macro levels. The study emphasises SCE’s profound impact on mental health and self-esteem at the micro level, revealing numerous benefits for individual students. On the macro level, the investigation expands to consider school-wide and broader life circumstances, shedding light on the multifaceted aspects influencing participation, motivation, and outcomes in the context of lifelong learning.