Recurrent involuntary autobiographical memories (IAMs) are memories retrieved unintentionally and repetitively. We examined whether the phenomenology and content of recurrent IAMs could differentiate boredom and depression, both of which are characterized by affective dysregulation and spontaneous thought. Participants (n = 2484) described their most frequent IAM and rated its phenomenological properties (e.g., valence). Structural topic modeling, a method of unsupervised machine learning, identified coherent content within the described memories. Boredom proneness was positively correlated with depressive symptoms, and both boredom proneness and depressive symptoms were correlated with more negative recurrent IAMs. Boredom proneness predicted less vivid recurrent IAMs, whereas depressive symptoms predicted more vivid, negative, and emotionally intense ones. Memory content also diverged: topics such as relationship conflicts were positively predicted by depressive symptoms, but negatively predicted by boredom proneness. Phenomenology and content in recurrent IAMs can effectively disambiguate boredom proneness from depressive symptoms in a large sample of undergraduate students from a racially diverse university.