<p>Helicopter parenting can detrimentally impact college student outcomes. This study examined whether two forms of entitlement (psychological and academic) explained associations between helicopter parenting and academic well-being and school engagement in two samples of college students. Data was collected from 638 students prior to the COVID-19 pandemic (Study 1) and 637 students after universities resumed in-person classes after the onset of the pandemic (Study 2) and analyzed separately. In both studies, helicopter parenting was negatively associated with academic well-being and school engagement through academic entitlement (externalized responsibility). Differences between studies emerged such that helicopter parenting was associated with academic-related outcomes through both psychological entitlement and academic entitlement (entitled expectations) only in the post-onset of COVID-19 sample. Psychological entitlement was associated with better academic well-being and school engagement in models, contrary to hypotheses. We suggest ways these findings can be incorporated into interventions designed to address helicopter parenting and support college students.</p>