This study investigated to what extent career decision-making difficulties (CDMD) impact students’ satisfaction with life and the potential mediating and moderating role of career choice support in this relation among 1094 grade 12 students in Ontario, Canada. Findings supported the negative impact of CDMD on students’ life satisfaction. Surprisingly, unlike counselors’ support, only teacher and parental support were significant drivers of students’ life satisfaction, with parental support exhibiting a solid effect. Furthermore, although support from each stakeholder partially mediated between CDMD and life satisfaction, parental support was identified as the strongest in reducing the negative impact of difficulties on students’ life satisfaction. Moderation effects were not supported.