While pupil-initiated cyberbullying of school staff is of growing concern, it remains under-investigated. This study adopts a mixed-methods approach to advance understanding of the underlying factors that increase the risk of school staff being victimised by pupils. We draw on findings from a Swedish case study comprising a focus group interview with pupils and in-depth interviews with teachers and school leaders to develop relevant hypotheses. These hypotheses were tested using a sample of 73,821 teachers and school leaders in Germany, examining personal characteristics and work-environment factors associated with an increased risk of being targeted. The analysis indicates that exposure to cyberbullying was particularly prevalent among lower secondary school teachers, and it increased with higher quantitative demands, role conflict, and greater levels of conflict with parents. Conversely, stronger parental support and common educational visions functioned as protective factors. These findings highlight considerable scope for targeted interventions.