BACKGROUND Stopping the epidemic of e-cigarette use among youth has become the common goal of both regulatory authorities and health departments. JUUL is currently the most popular e-cigarette brand on the market. Young people usually obtain and exchange information about JUUL with the help of social media platforms. Along with the rising prevalence of JUUL, posts about underage JUUL buying and selling have appeared on social media platforms such as Reddit, which sharply increase the risk of minors being exposed to JUUL. OBJECTIVE This study aims to analyze Reddit messages about JUUL buying and selling among the users of the UnderageJuul subreddit, and to further summarize the characteristics of those messages. The findings and insights can contribute to a better understanding of the patterns of underage JUUL use, and help public health officials provide timely education and guidance to minors who have intentions of accessing JUUL. METHODS We used a novel cross-subreddit method to analyze the Reddit messages on 2 subreddits. From July 9, 2017, to January 7, 2018, we collected data from the UnderageJuul subreddit, which was created for underage JUUL use discussion. The data set included 716 threads, 2935 comments, and 844 Reddit users (ie, Redditors). We collected our second data set, comprising 23,840 threads and 162,106 comments posted between July 9, 2017, and January 8, 2019, from the JUUL subreddit. We conducted analyses including the following: (1) annotation of users with buying/selling intention, (2) posting patterns discovery and topic comparison, and (3) posting activeness observation of discovered Redditors. Term frequency–inverse document frequency and regular expression-enhanced keyword search methods were applied during the content analysis to extract the posting patterns. The public posting records of the discovered users on the JUUL subreddit during the year after the UnderageJuul subreddit was shut down were analyzed to determine whether they were still active and interested in obtaining JUUL. RESULTS Our study revealed the following: (1) Among the 716 threads on the UnderageJuul subreddit, there were 214 threads related to JUUL sale and 168 threads related to JUUL purchase, which accounted for 53.5% (382/714) of threads. (2) Among the 844 Redditors of the UnderageJuul subreddit, 23.82% (201/844) of users were annotated with buying intention, and 21.10% (178/844) of users were annotated with selling intention. There were 34 users with buying/selling intention that self-reported as being CONCLUSIONS There were overlapping users active in the JUUL and UnderageJuul subreddits. The buying/selling-related content appeared in multiple venues with certain posting patterns from July 9, 2017, to January 7, 2018. Such content might lead to a high risk of health problems for minors, such as nicotine addiction. Based on these findings, this study provided some insights and suggestions that might contribute to the decision-making processes of regulators and public health officials.