The Digital Age has created massive technological and disciplinary shifts in tabletop role-playing, increasing the appreciation of games like Dungeons & Dragons. Millions tune in to watch and listen to RPG players on podcasts and streaming platforms, while virtual tabletops connect online players. Such shifts elicit new scholarly perspectives. This collection includes essays on the transmedia ecology that has connected analog with digital and audio spaces. Essays explore the boundaries of virtual tabletops and how users engage with a variety of technology to further role-playing. Authors map the growing diversity of the TRPG fandom and detail how players interact with RPG-related podcasts. Interviewed are content creators like Griffin McElroy of The Adventure Zone podcast, Roll20 co-creator Nolan T. Jones, board game designers Nikki Valens and Isaac Childres and fan artists Tracey Alvarez and Alex Schiltz. These essays and interviews expand the academic perspective to reflect the future of role-playing.