Over the last few years, there have been an increasing number of gaming operators that have incorporated on-screen pop-up messages while gamblers play on slot machines and/or online as one of a range of tools to help encourage responsible gambling. Coupled with this, there has also been an increase in empirical research into whether such pop-up messages are effective, particularly in laboratory settings. However, very few studies have been conducted on the utility of pop-up messages in real-world gambling settings. The present study investigated the effects of normative and self-appraisal feedback in a slot machine pop-up message compared to a simple (non-enhanced) pop-up message. The study was conducted in a real-world gambling environment by comparing the behavioral tracking data of two representative random samples of 800,000 gambling sessions (i.e., 1.6 million sessions in total) across two conditions (i.e., simple pop-up message versus an enhanced pop-up message). The results indicated that the additional normative and self-appraisal content doubled the number of gamblers who stopped playing after they received the enhanced pop-up message (1.39%) compared to the simple pop-up message (0.67%). The data suggest that pop-up messages influence only a small number of gamblers to cease long playing sessions and that enhanced messages are slightly more effective in helping gamblers to stop playing in-session.