Background/Objectives: Operational Assistants (OAs), as non-teaching staff responsible for playground supervision and school hygiene, play a vital role in ensuring safe and well-organized school environments. Despite their importance, research on their working conditions, job satisfaction, and well-being remains limited. This study aims to examine the quality of work life (QoWL) and job satisfaction (JS) of OAs in public schools in the Municipality of Setúbal, Portugal, and to explore their relationship with absenteeism. Methods: A quantitative research design was adopted using a survey questionnaire administered to Operational Assistants (N = 119). Data were collected on QoWL, job satisfaction, and absenteeism indicators to assess patterns and relationships among these variables. Results: Findings indicate that OAs experience significant challenges related to working conditions and health risks, which are associated with higher levels of absenteeism. Nonetheless, many participants report valuing the stability associated with public-sector employment. Conclusions: The results highlight the need for targeted interventions, including improved working conditions, enhanced training, and mental health support, to reduce absenteeism and promote employee well-being. This study contributes to a better understanding of an often-overlooked workforce and offers practical implications for policymakers and school administrators aiming to foster more supportive and sustainable school environments.