Theoretically, there are strong arguments for a relationship between cyberbullying and trust. On the one hand, trust is built on experiences; thus, experiences of malevolence such as cyberbullying might contribute to low trust. On the other hand, high trust may lead to risky online behavior such as self-disclosures that could increase the risk of cyberbullying. As first empirical evidence, we explored this relationship in two cross-sectional studies. Explorative Study 1 (N?=?224) showed that negative experiences of family problems and cyber-perpetration predicted low generalized trust. Exploratory Study 2 (N?=?196) showed no significant direct relationship, but trust was related to low online privacy concerns and the willingness to self-disclose online was positively related to cyber-victimization and cyber-perpetration. Thus, these studies show mixed evidence and demonstrate that the relationship between cyberbullying and trust might be more complex than assumed. Future longitudinal designs might be illuminating.