In the Italian education system, pupils with special education needs (SEN) are fully included in mainstream education and receive extra support from special education teachers (SET). Starting from this point, it is reasonable to expect some degree of difference between special education teachers (SETs) and general education teachers (GETs) in term of occupational stress stemming from job demands as well as students' challenging behaviours. The study explored the connection between "students' challenging behaviours" and "teachers' occupational stress" in a sample of Italian inservice primary teachers (N = 306). Data from the Italian version of the "Challenging Students Standard Questionnaire" were analysed to understand the impact of six different categories of "challenging students' behaviours" on eliciting "occupational stress" responses in SETs and GETs. Descriptive, comparative t-test analyses and effect sizes for all measures were reported. Results were consistent with the idea that SETs and GETs experience different degrees of occupational stress as a result of experiencing different "challenging students' behaviours." Recommendations for planning more targeted in-service training for primary teachers are discussed. (Contains 4 tables.)