This session will explore the various factors motivating players of Dwarf Fortress, a self-consciously unapproachable, unforgiving, and unwinnable game that has nevertheless managed to attract a dedicated fanbase whose motto is “Losing is fun.” The game, centered around ordering a group of dwarves to build a settlement to ensure their own survival, features an inscrutable ASCII art design, abstruse user interface, no tutorial, and the inability to restart from a prior saved game upon being defeated. In spite of all of this, Dwarf Fortress has developed a cult following since its release in 2006. We will consider why that is, and in particular the motivational impetus of learning from one’s mistakes, the appeal of existing within a procedurally generated world and contributing to its intricate history, and the nearly unprecedented freedom afforded players by the game’s fully open-ended sandbox format.