<p>Although work engagement is recognised as a key state influencing staff well-being and performance, educational research has often prioritised organisational factors, overlooking individual-level variables. This study addresses this gap by examining individual characteristics among staff working in Alternative Provision settings (APs), such as Pupil Referral Units (PRUs) and hospital education services across England. This research investigated the relationships between life satisfaction (SWL), perceived stress (PS), proactive personality (PPS), and work engagement (Vigour, Dedication, Absorption). Proactive personality was conceptualised as a relatively stable personal trait, whereas life satisfaction, perceived stress, and work engagement were treated as context-dependent states or attitudes. A total of 101 current teachers and support staff were recruited with assistance from the National Association of Hospital Education and the PRUs Organisation (PRUsAP). Data were collected using validated scales for each construct, and multiple regression and moderation analyses were conducted. Key findings revealed that life satisfaction and proactive personality were significant positive predictors of all three dimensions of work engagement. Conversely, perceived stress negatively predicted vigour and dedication. Importantly, proactive personality moderated the relationship between life satisfaction and vigour: for educators with lower proactivity, higher life satisfaction was strongly associated with increased vigour, an effect that diminished as proactive personality increased. The full models accounted for substantial variance—57% in vigour, 31% in dedication, and 40% in absorption. These findings suggest that interventions aimed at enhancing life satisfaction may be especially beneficial for staff less naturally inclined towards proactive behaviour. The results highlight the value of recognising individual differences in promoting well-being and engagement in alternative educational contexts.</p>