Diplomacy is a strategy board game enjoyed for its emphasis on execution of strategy through negotiation with other players. However, its long gameplay means that interruptions are likely to occur, raising cognitive challenges for the players of the game. This project inspects this issue through the critical lens of human computer interaction, game design and cognitive psychology to explore the role of board game companion applications in supporting the prospective memory, motivation, and self-efficacy of Diplomacy players who are resuming an interrupted game of Diplomacy.