This study examined the indirect effects of distinct aspects of invalidating caregiving environments (i.e., paternal maltreatment, maternal maltreatment, and perceived alienation) on non-suicidal self-injury (NSSI) via six specific emotion regulation difficulties. We hypothesized that specific emotion regulation deficits would mediate associations between invalidating environments and NSSI. Participants included 114 young adults (57 self-injurers; 57 age- and sex-matched comparison participants) aged 17–25 years. Three parallel mediation models tested hypotheses. Results showed that maternal maltreatment, paternal maltreatment, and perceived alienation indirectly predicted NSSI through poor emotional clarity. Maternal maltreatment uniquely predicted NSSI through limited access to regulation strategies. Lastly, maternal maltreatment and perceived alienation were both linked to greater difficulties engaging in goal-directed behavior during emotional upsets; however, contrary to hypotheses, this particular deficit was associated with decreased odds of engaging in NSSI. Findings illustrate how different aspects of invalidating environments and specific emotion regulation deficits may be implicated in NSSI engagement.