Recent scientific attention has focused on the therapeutic effectiveness of cannabis use on a variety of physical and mental ailments. The present study uses smartphone technology to assess self-reported experiences of Florida cannabis users to understand how cannabis may impact anxiety and depression symptomatology. Several hundred Releaf App™ users from the state of Florida provided anonymous, real-time reports of their symptoms of anxiety and/or depression immediately before and after cannabis use sessions. Linear mixed-effects modeling was used to analyze the data at the symptom and user level. Results showed that for the majority of users, cannabis use was associated with a significant decrease in depression and anxiety symptomatology. While symptom type, doses per session, consumption method, and CBD levels were significant predictors of relief change, their effect sizes were small and should be interpreted with caution. At the user level, those who had positive relief outcomes in anxiety reported more doses and sessions, and those in the depression group reported more sessions. Our results generally support the therapeutic effectiveness of cannabis against depression/anxiety symptomatology. Future work should include standardized statistics and effect size estimates for a better understanding of each variable's practical contribution to this area of study.