Students’ worries about transitioning to college are correlated with long-term reduced psychological well-being, so we investigated how psychological need satisfaction might mitigate millennials’ worries about college. As parents can support or undermine their children’s basic needs, we also examined the influence of autonomy-supportive and helicopter parenting during the transition. Additionally, we compared these outcomes between first- and continuing-generation students. Incoming college students (N = 355) completed measures of parental relationship need satisfaction, parental involvement, worries about college, and family achievement guilt. Higher need satisfaction in the parental relationship was associated with reduced worries and feelings of achievement guilt for both first- and continuing-generation students. Autonomy-supportive parenting moderated the relationship between autonomy and millennials’ worries about college. Helicopter parenting did not moderate any of the relationships examined in this study but was positively associated with students’ transition worries and achievement guilt. We discuss these findings in the context of self-determination theory.