A comparison of two experimental games that each attempt to scaffold the first year university experience. "Just Press Play," from RIT, an achievement-based system that encourages students to think of the obstacles in their path as part of a narrative of their educational development. "Reality Ends Here," from USC, is a DIY media-making ARG that introduces students to the culture and history of the cinema school, challenging them to become part of the school's storied tradition. Designers and evaluators from each team discuss learning goals, design strategies, assessment approaches, preliminary outcomes and next steps for these innovative digital learning environments.