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Introduction: Different studies confirm a stronger link between maladaptive personality traits and Non-suicidal Self-injury (NSSI). Additionally, the interest in the relationship between the experience of the COVID-19 pandemic and NSSI is growing. The present study aims (a) to investigate differences in personality traits between individuals with NSSI, suicidal ideation, NSSI and suicidal ideation co-occurrence and none; (b) to observe which personality traits predominantly influence the occurrence of self-harm acts; (c) to evaluate the difference in self-harm attitudes pre and post COVID-19 pandemic. Method: 270 (108 males and 162 females) participants aged between 18 and 25 were included in the study. Everyone participated in a clinical interview and completed an assessment consisting of the Personality Inventory for DSM-5 (PID-5) and the Health of the Nation Outcome Scales (HoNOS). A multivariate analysis of variance (MANOVA), a multiple hierarchical regression analysis, controlling for age and gender and a T-test for independent samples were conducted. Results: The individuals with the highest levels of negative affectivity, detachment, antagonism, and psychoticism are those who simultaneously present suicidal ideation and NSSI. Moreover, age and detachment predicted higher scores in self-harm attitudes. Our results unexpectedly do not confirm an upward trend of NSSI and suicidal ideation during the pandemic period. Limitations: The study is cross-sectional, and no causal links can be assumed; the groups involved were not homogeneous for numerosity. Conclusions: The results testify that the study of maladaptive traits is fundamental to a greater understanding of NSSIs. Working clinically on those could potentially reduce.