Purpose: Colorectal redo surgery is well known to be a difficult procedure, associated with a high risk of failure. The aim of this study was to look into patients presenting two consecutive failed colorectal (CRA) or coloanal (CAA) anastomosis who underwent a second redo surgery (i.e., third anastomosis). Methods: A retrospective study based on a prospective database of second redo surgeries of CRA or CAA, in an expert center. Sixteen patients between 2005 and 2020 were analyzed. Results: After a mean follow-up of 28 ± 26 months, success of surgery (defined as no stoma at the end of follow-up) was reported in 10/16 patients (63%). One patient with chronic anastomotic leakage and another with early colonic ischemia had no defunctioning stoma reversal. In the remaining four patients with a failed second redo surgery, a definitive stoma was ultimately created for fistula recurrence (n = 1), poor functional results (n = 2), or local cancer recurrence (n = 1). Two risk factors for failure of this second redo surgery were significantly found in a univariate analysis: (1) nature of the primary anastomosis: 3/13 s redo surgeries failed (23%) if a CRA was first made and 3/3 (100%) if it was a CAA (p = 0.036); (2) age: patients with a failed second redo surgery were older (p = 0.04). Conclusion: A 63% rate of success of second redo surgery was observed after two failed CRA or CAA. Although a demanding procedure, it can be proposed to carefully selected and motivated patients.