While time travel as a narrative device has been firmly entrenched in popular culture since the late 19th century, its sub-trope, the time loop, has been largely neglected until the 1990s. Star Trek, never a franchise to shy away from bold narrative tools, first introduced a time loop in the Star Trek: The Next Generation episode “Cause and Effect” (1992). Since then, the trope has become a well-known storytelling device, especially within the realms of science fiction television series. A time loop occurs when the temporal fabric of a narrative world enfolds one or several characters in a recurring circular loop, while for the rest of the story world, time flows in its natural direction. Most crucial in many of these narratives is the question of emotional development and human connection, both equally enabled and denied by the time loop. This is also the case in Discovery’s seventh episode “Magic to Make the Sanest Man Go Mad” (2017). This chapter looks at the episode, at the special narrative space created by the time loop, the counterfactuals it generates, and the emotional development it affords to the characters trapped inside – and outside.