Numerous studies have examined how youth are influenced by the presence of tobacco retail outlets that use point-of-sale marketing tactics to promote nicotine and tobacco products. The current investigation extends this research by assessing whether tobacco retail outlets function as environmental cues that prompt associative memories linked to the repeated use of cigarettes, electronic cigarettes, and cigars. Students (N = 1060) from 29 alternative high schools in California were recruited into a three-year cohort study. A repeated measures latent profile analysis was conducted to identify latent subgroups of students. Analyses suggested the presence of one subgroup of students that did not use nicotine and tobacco products and five subgroups of students that used multiple products. A multinomial logistic regression revealed that images of gas stations, convenience stores, and liquor stores presented in the first year of the study prompted spontaneous associations in memory that increased the odds a student would belong to one of the five subgroups that repeatedly used nicotine and tobacco products over a three-year period. These findings suggest that tobacco retail outlets may act as environmental cues that prompt the use of addictive products among at-risk youth. Policymakers should consider implementing strategies that reduce the potency and prevalence of these cues.