The ability to communicate effectively is critical in the accounting profession, yet research shows there is a gap between employer expectations and student abilities to adapt communication to various contexts. In this paper we introduce “Communication Roulette,” a novel learning intervention that encourages students to practice their written communication skills by sensitizing them to the need to tailor their message to different audiences using various communication formats while simultaneously reinforcing their knowledge in important content areas. Survey results indicate Communication Roulette increases student confidence and perceived ability to communicate effectively with different audiences and formats. These improvements can largely be achieved through peer feedback alone, although we document incremental improvements with instructor feedback. Finally, we document an improvement in student content knowledge following Communication Roulette.