It has been argued that generating pop-up messages during electronic gambling sessions, which cause a player to engage in self-appraisal of their gambling behaviour, instil greater control and awareness of behaviour (Monaghan, Computers in Human Behaviour, 25, 202–207, 2009). Consideration for the potential interaction between the messaging’s efficacy and gambling outcome (winning or losing) is lacking however. Thirty participants took part in a repeated-measures experiment where they gambled on the outcome of a computer-simulated gambling task. Outcome was manipulated by the experimenter to induce winning and losing streaks. Participants gambled at a significantly faster speed and a higher average stake size, which resulted in a greater betting intensity in the Loss condition compared to the Win condition. Computer generated self-appraisal messaging was then applied during the gambling session, which was able to significantly reduce the average speed of betting in the Loss condition only, demonstrating an interaction effect between computer generated messaging and gambling outcome.