Under the name Rebecca Sean Borgstrom (and sometimes simply as 'R'), Jenna began making her presence known in online RPG communities. She quickly gained a reputation for insightful commentary, sharp wit, and a distinct perspective on game design. This period marked the genesis of her engagement with the hobby, laying the groundwork for her future career. She contributed to various online discussions and helped foster a sense of community that would later support her independent projects.

Jenna's first major RPG work, "The Shab-al-Hiri Roach", was released. This game, notable for its intricate setting, challenging gameplay, and unique approach to character relationships, immediately established her as a designer to watch. The game's blend of dark humor, existential dread, and innovative mechanics resonated with many indie RPG enthusiasts, cementing her place within the community. It is still played today and talked about in hushed tones as to its complexity, intrigue, and challenging gameplay.