Background: Few studies have described youth cigarette sources in terms of whether the cigarettes were free or purchased. Understanding the different ways youth obtain tobacco can guide development of interventions to more effectively reduce youth smoking. Purpose: To determine the propensity for youth to purchase cigarettes versus obtain cigarettes for free, and the factors associated with each obtainment method. Methods: Our sample included 812 youth ages 12-17 who reported ever smoking a whole cigarette. Our outcome was the source of the last cigarette smoked (purchased vs. free) and independent variables included demographics, smoking behaviors, and smoking status of parents/siblings/friends. We conducted logistic regression to assess relationships between outcome and independent variables. Results: Eighty-four percent of youth obtained their last cigarette for free and 16% purchased their last cigarette. Youth who smoked less and had less weekly spending money were more likely to have obtained their last cigarette for free. Discussion: Youth smokers appear to have a high propensity to obtain their cigarette for free, particularly those who smoke relatively infrequently. Translation to Health Education Practice: Interventions that target sources of free cigarettes have the potential to reduce the progression of youth smoking at a critical stage in its development.