Tabletop exercises are often a boring compliance checkbox to fill which can offer varying levels of effectiveness. A well-thought-out scenario with an engaging and exciting tabletop exercise is far more effective than anything required from a compliance framework. There is a deceptively large overlap of skills required for running Dungeons and Dragons (D&D) and an effective cyber security tabletop exercise. Colby will show a unique perspective on running more effective tabletop exercises using knowledge from games like Dungeons and Dragons.The talk will initially focus on the overlap of D&D and tabletop exercises followed by key lessons on good scenario design: • Supporting player agency by removing railroads • Understanding actor motivations • Building a narrative • How to document a complex scenario The second half of the talk will focus on skills developed at the table from dungeon masters running a smooth scenario: • Leading with principals and following with rules • How to share the table spotlight in a diverse group • Tricks for keeping things flowing instead of getting stuck in a bog • How to handle non-linear and collaborative storytelling • Anyone attending this talk will walk away with tangible techniques they can use to make their next tabletop exercise both more fun and more effective.