Objective: To evaluate if a remote digital monitoring system added at the end of orthodontic treatment could positively influence the retention phase by reducing the occurrence of misfit of removable appliances, number of emergency appointments (EA), and orthodontic relapse. Methods: Twenty-seven patients who completed active orthodontic treatment were divided into the study and control groups. In addition to the standard chairside follow-up appointments at month 1 (T1), month 3 (T2), month 6 (T3), the study group patients were monitored using Dental Monitoring® with monthly intra-oral scans. Occurrence of misfit of removable retainers, number of EAs, and intercanine width change were recorded for both groups. Differences in EAs and retainer fit were assessed using the chi-square test. Intra-group and inter-group differences in the intercanine width were assessed with Friedman test and Mann–Whitney U test, respectively (α = 0.05). Results: The study group showed a significantly lower occurrence of misfit of removable retainers (p = 0.027) compared to the control group. No significant inter- and intra-group difference was found in the EAs and intercanine width change at each time-point. Conclusions Integrating remote monitoring systems, such as Dental Monitoring® , to the retention phase of the orthodontic treatment may lower the occurrence of misfit of removable retainers. However, a small sample size and a short observation period limit the strength of this evidence. These preliminary results tentatively suggest that remote monitoring technologies may be beneficial, especially during the COVID-19 pandemic, when the regularity of in-office visits might be disrupted.