Introduction Telehealth has demonstrated reduced cost and increased satisfaction post-operatively compared to Conventional Follow-up (CFU). However, a Flexible Care Pathway (FCP), which involves only "as-needed" follow-up, has never been formally evaluated. We hypothesize that the FCP is a safe and satisfactory for patients who undergo carpal (CTR)/ cubital tunnel release (CuTR). Materials and Methods Preoperatively, veterans were given the option to enroll in the FCP, in which post-operative followup visits were "as-needed" only. Patients who chose CFU were evaluated within 2 weeks post-operatively. Preoperatively, detailed post-operative instructions were given to both groups. Both groups were contacted by phone 30 days post-operatively with a questionnaire. The main outcomes were the number of FCP to CFU conversions, complications, time and distance of patient travel, and patient satisfaction. Results 105 patients were enrolled in the study, 60.2% chose FCP. One quarter (23.7%) of patients in the FCP group returned for in-person clinic evaluation. On average, the CFU group travelled a roundtrip distance of 102.9 miles and expended 3.51 h for their follow-up visits. CFU patients ranked their satisfaction at an average of 8.6/10, FCP patients ranked an average of 9.5/10 (p < 0.05). Conclusions The FCP can be used in ambulatory hand surgeries with a high degree of safety and satisfaction, studied up to 30 days post-operatively. The FCP demonstrated higher patient satisfaction and a decrease in patient travel than CFU. This is particularly relevant in geographically broad areas, in populations with less access to specialty care, and in a pandemic where contact is limited.