Until now, IT-Security Tabletop Games for developers only existed in analog format, but with the pandemic, interest in collaborative remote security games has increased. In this paper, we propose a methodology to evaluate the impact of a (remote) security game-based intervention on developers. The study design consists of the respective intervention, three questionnaires, and a small open interview guide for a focus group. An already validated scale for developers’ self-efficacy is embedded in the questionnaires and it is used as a proxy for measuring effects on participants’ ability to develop secure software. In addition, we tested this design with 9 participants (expert and novice developers and security experts) as part of a small feasibility study focusing on the challenges and limitations of remote tabletop games. We describe an initial selection and digitization of three security tablet-top games and we report our first qualitative findings. The setting up and running of virtual tabletop games turned out to be challenging and complex for the moderator and the participants and required patience and persistence. We also found limitations of the social interaction in the remote setting. Our findings can be helpful in building and evaluating a better, more comprehensive, technically sound and issue-specific game-based training measure for developers. The methodology can be used by researchers to evaluate existing and new game designs, and identify improvements.