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The COVID-19 pandemic posed unprecedented challenges, requiring compliance with public health measures. Notably, guilt is a powerful motivator for rule adherence; however, different types of guilt could have fueled the decision to stay home. This study investigated how guilt propensity influenced Italians’ self-reported motivations for adhering to containment rules. The propensity to different types of guilt, namely deontological and altruistic, was assessed in a total of 393 participants (261 females, 66.4%; 132 males, 33.6%; M age = 34.4, SD = 12.6) in May 2020, between the first and the second phases of Italian lockdown. The survey assessed four guilt dispositions—Moral Norm Violation (MNV), Moral Dirtiness (MODI), Harm-based guilt (HARM), and Empathy-based guilt (EMPATHY)—alongside fear of COVID-19, trust in authorities, and motivations for rule compliance (e.g., protecting one’s own and others’ well-being, respecting authorities, and avoiding sanctions). MNV emerged as a positive predictor of prosocial, authority-based and personal motivations, whereas MODI predicted lower prosocial motivation. HARM selectively predicted prosocial motivation and was negatively associated with authority-based motivations, while EMPATHY negatively predicted self-focused motivations. Moderation analyses revealed small but significant interaction effects, indicating that fear of COVID-19 slightly amplified the influence of EMPATHY and attenuated the effect of HARM, whereas trust in authorities strengthened the link between EMPATHY and prosocial compliance and reduced the association between MNV and prosocial motivations. These findings suggest that compliance during the pandemic was shaped by distinct emotional–moral pathways and that the motivational impact of guilt depends on perceived threat and institutional trust, highlighting the relevance of specific guilt profiles in promoting cooperative and health-protective behaviors.