Background: Truck drivers constitute a high-risk occupational group due to irregular schedules, prolonged sedentary work, fatigue, and limited access to healthcare, contributing to adverse physical and mental health outcomes. Although mobile health (mHealth) tools offer potential to support driver health, sustained engagement remains a persistent challenge. Objectives: This systematic review aimed to identify behavioural, technological, and contextual determinants influencing truck drivers’ compliance, retention, and long-term engagement with digital health interventions. Methods: Following the PRISMA 2020 guidelines, six eligible studies were identified and thematically synthesised across technology acceptance, behaviour change, and persuasive system design perspectives. Results: Across studies, sustained engagement was facilitated by self-monitoring, real-time feedback, goal-setting, coaching support, and simple, flexible system design. In contrast, technological complexity, high interaction demands, limited digital literacy, privacy concerns, misalignment with irregular schedules, and fatigue consistently undermined engagement and retention. Autonomy, trust, and voluntary participation emerged as cross-cutting determinants supporting continued use. Based on the synthesis, an integrative framework was developed to explain how behavioural, technological, and contextual factors interact to shape truck drivers’ compliance, engagement, and retention with mHealth. Despite generally moderate to high study quality, the evidence base remains fragmented and dominated by short-term evaluations. Conclusions: The findings highlight the importance of context-sensitive, user-centred design to support effective digital health interventions in the trucking sector.