We show that familiarity between lawyers and judges accelerates case resolution in corporate bankruptcies by 15%. Familiarity developed through repeated in-court interactions, where lawyers gain first-hand knowledge of judges' preferences, is more valuable than connections through educational or professional networks. Familiar lawyers manage cases more efficiently by filing fewer motions, maintaining a consistent filing pattern, and securing faster judicial approvals. Firms represented by familiar lawyers incur lower professional fees, primarily due to retaining fewer legal professionals, and creditors in these firms recover more. Our findings highlight the value of familiarity in repeated transactions where channels for private communication are limited.