The Objective Structured Clinical Examination (OSCE) is a commonly utilized modality to assess learner clinical skills in a simulated environment. It is important that OSCE cases are well written; A poorly constructed case can frustrate the learner, lack realism, and lead to disrupted narrative flow. An ideal response process in an OSCE case, or for any assessment, takes the learner to the patient’s bedside or puts them into the cognitive and affective state similar to that of clinical work. There are several parallels between writing OSCEs and creating Dungeons and Dragons (D&D) adventures. From determining the central conflict to designing D&D adventures using the classic three part structure, from creating challenging yet solvable challenges to distributing loot and treasure, the approaches and lessons of being a DM align with being an OSCE case writer.