In an ageing society, the at-home use of Socially Assistive Robots (SARs) could provide remote monitoring of their users’ well-being, together with physical and psychological support. However, private home environments are particularly challenging for SARs, due to their unstructured and dynamic nature which often contributes to robots’ failures. For this reason, even though several prototypes of SARs for elderly care have been developed, their commercialization and widespread at-home use are yet to be effective. In this paper, we analyze the impact of introducing a novel web-based Monitoring and Logging System (MLS) on the SARs reliability and user acceptance. This monitoring framework, specifically designed for remote supervision and control of SAR-based systems in older adults’ apartments, also allows exchanging feedback between caregivers, technicians, and older adults, to better explain the SAR-based systems’ behaviours. The MLS was developed, tested, and evaluated within the pilot study of the H2020 project MoveCare, where 13 autonomous SARs were deployed in the house of older adults living alone and remotely monitored for over 180 weeks. The results from this field trial suggest that the use of the MLS during the pilot increased the acceptance of the SAR-based system in the event of failures and anomalies.