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Continuous positive airway pressure (CPAP) telemonitoring (TMg) has become widely implemented in routine clinical care. Objective measures of CPAP compliance, residual respiratory events, and leaks can be easily monitored, but limitations exist. This review aims to assess the role of TMg in CPAP-treated obstructive sleep apnea (OSA) patients. We report recent data related to the accuracy of parameters measured by CPAP and try to determine the role of TMg in CPAP treatment follow-up, from the perspective of both healthcare professionals and patients. Measurement and accuracy of CPAP-recorded data, clinical management of these data, and impacts of TMg on therapy are reviewed in light of the current literature. Moreover, the crucial questions of who and how to monitor are discussed. TMg is a useful tool to support, fine-tune, adapt, and control both CPAP efficacy and compliance in newly-diagnosed OSA patients. However, clinicians should be aware of the limits of the accuracy of CPAP devices to measure residual respiratory events and leaks and issues such as privacy and cost-effectiveness are still a matter of concern. The best methods to focus our efforts on the patients who need TMg support should be properly defined in future long-term studies.