This essay analyzes the subtle theology of laughter that is scattered across Augustine’s Confessiones (conf.). First, I draw on Sarah Byers’s work in order to argue that Augustine adopts and adapts Stoic moral psychology as a means of sorting the laugh into two moral kinds—as evidence of either good joy or bad joy. In turn, these two kinds provide the loose structure for the double theological taxonomy of merciless and merciful laughter that conf. develops. Next, I treat laughter of each sort via exegesis of several textual vignettes. Close readings of key passages show that both merciless and merciful laughter evince distinctive features across Augustine’s conf. This also reveals exactly how Augustine embeds laughter’s double taxonomy in order to confect his own salvation narrative. Thus, on the reading offered here, laughter proves central to the salvation history that Augustine’s conf. weaves. We learn a good deal about Augustine’s story and his theology by attending to the subject, object, and character of laughter that may be found in his conf.