Drawing on a corpus of telephone conversational data, this study examines a collection of self-deprecations in Korean conversations. Detailed analyses of self-deprecations in larger fragments than minimal adjacency pair sequences illustrate the multifaceted nature of self-deprecation. Self-deprecation entails not only deprecatory assessments, but complaint or trouble talk about one’s shortcomings, reenactment of experiences or moments that support the deprecation, and discussion of how to remedy problems. The study further shows that self-deprecation is not a solitary but an interactionally organized practice. The speaker’s repeated self-deprecations elicit a series of different responses from the recipient, such as positive reframing, downgrading the deprecator’s problem, and recommending solutions to the deprecator’s problem. Many instances of self-deprecation suggest that it can be an important resource for building motivation, responsibility, and a sense of affiliation and solidarity with other social members.