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Background We have anecdotally noticed a higher rate of trigger fingers (TFs) developing in patients who have undergone carpal tunnel release (CTR). Questions/Objective Is the rate of TFs after CTR greater compared to the nonoperative hand? Is the thumb more commonly involved postoperatively compared with spontaneous TFs? Do particular associated comorbidities increase this risk? Patients and Methods We queried our institutional database for patients who had undergone open CTR during a 2-year period and recorded the development of an ipsilateral TF after a CTR or a contralateral TF in the nonoperative hand. Patient demographics, comorbidities, concurrent initial procedures, time to diagnosis, and finger involvement were recorded. Results A total of 435 patients underwent 556 CTRs during this period. Furthermore, 46 ipsilateral TFs developed in 38 of 556 cases (6.83%) at an average of 228.1 ± 195.7 days after surgery. The thumb was most commonly involved (37.0%) followed by the ring finger (28.3%). The incidence rate of TF in the nonoperative hand during this period was 2.7%, with the ring finger and middle finger most commonly involved (33.3 and 28.6%, respectively). Only history of prior TF in either hand was found to be a significantly associated on Chi-square analysis and multivariable regression (p Conclusion In patients with carpal tunnel syndrome, ipsilateral TFs occurred after 6.83% of CTRs, compared with a rate of 2.7% in the nonoperative hand, making it an important possible outcome to discuss with patients. The thumb was more commonly involved in triggering in the surgical hand compared with the nonoperative hand. Patients with a history of prior TFs in either hand were more likely to develop an ipsilateral TF after CTR. Level of Evidence This is a Level III, retrospective study.