As many cigarette smokers begin experimenting before age 16, prevention efforts require a comprehensive understanding of smoking predictors during adolescence. Research has made many advances in understanding the predictors of smoking initiation, yet more precision is still needed to determine whether the patterns of prediction differ across early smoking milestones. The purpose of this study was to use a sample of young adolescents to examine the predictors of two key milestones in smoking initiation: first puff and first cigarette. Data came from an ongoing, prospective project examining psychosocial factors related to adolescent substance use. At Time 1 (T1), the sample was 1,023 Rhode Island middle school students (ages 10-15 years; M = 12.2). T1 measures included empirically supported risk and protective factors, as well as current smoking. Follow-up surveys assessed smoking behavior over the ensuing year (T2 smoking). Cigarette availability was the most robust predictor of smoking milestones, increasing the likelihood of both first puff and first cigarette in cross-sectional and prospective analyses. Multivariable analyses also showed specificity, where some factors were only associated with one time point (e.g., age and T1 puff and cigarette), whereas others were only associated with one milestone (e.g., parental monitoring and whole cigarette at both time points). This study found different patterns of predictors for two early smoking milestones. Such findings are the first to suggest that puff and whole cigarette are distinct smoking milestones and reaffirm arguments that researchers should distinguish the various stages of smoking initiation when examining the broader period of onset/initiation.