This study explores the complex nature of failures within organizations, especially in project teams where individuals act as knowledge conduits. Despite the acknowledged importance of failure for organizational learning, a reluctance to share past failures due to social self-image remains prevalent. Grounded in self-disclosure theory, the research examines how disclosing past failures in new teams has dual effects on individuals’ perceived evaluation, peer acceptance, and performances. The study also develops a nuanced analysis of different disclosure approaches. Our empirical investigation, conducted through a survey of 364 employees in a dynamic organizational setting characterized by frequent inter-team transitions, sheds light on the dual nature of peer responses to failure disclosures. Findings reveal that such disclosures elicit both positive recognition and negative stigma from peers. The research also identifies the distinct moderating effects of descriptive and evaluative sharing on the benefits and costs of these disclosures. This investigation reveals the complexities of disclosing past failures, underscoring the balance between the benefits and drawbacks of such revelations, and deepening the understanding of failure disclosure dynamics within team-based organizational settings.