State dependent learning (SDL) occurs when learning acquired in one context is not retrievable in a different context. Although traditionally SDL is thought of in the context of substance use, the role of SDL should be considered during combined medication and exposure treatment for anxiety disorders. Data are presented from a within-subjects, case-series design of four participants with social anxiety disorder. Participants engaged in a series of situational exposures while taking either alprazolam (0.75 mg), propranolol (40 mg), placebo or no medication. They returned 48 h later and engaged in the same situational exposure in an unmedicated state to determine retention of learning following the shift in drug context. Results suggest that SDL effects are possible when combining pharmacotherapy (alprazolam) with exposure therapy. Future research is needed determine the conditions under which SDL is most likely to occur and ways to facilitate transfer of learning across different contexts.