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Introduction: Understanding the characteristics of experimental smoking among youth is critical for designing prevention programs. This study examined which student- and school-level factors differentiated experimental smokers from never smokers in a nationally representative sample of Canadian students in grades 9 to 12., Methods: School-level data from the 2006 Canadian Census and one built environment characteristic (tobacco retailer density) were linked with data from secondary school students from the 2008-2009 Canadian Youth Smoking Survey and examined using multilevel logistic regression analyses., Results: Experimental smoking rates varied across schools (p < .001). The location (adjusted odds ratio [AOR] = 0.66, 95% CI: 0.49-0.89) of the school (urban vs. rural) was associated with the odds of a student being an experimental smoker versus a never smoker when adjusting for student characteristics. Students were more likely to be experimental smokers if they were in a lower grade, reported low school connectedness, used alcohol or marijuana, believed that smoking can help people relax, received pocket money each week and had a family member or close friend who smoked cigarettes., Conclusion: School-based tobacco prevention programs need to be grade-sensitive and comprehensive in scope; include strategies that can increase students' attachment to their school; and address multi-substance use, tobacco-related beliefs and the use of pocket money. These programs should also reach out to students who have smoking friends and family members. Schools located in rural settings may require additional resources.