A system for proactively troubleshooting set top box issues may include a media distribution network with a remote requesting device and a programming guide server. The programming guide server may be configured to identify a guide data retrieval profile of the requesting device, compare the guide data retrieval profile to an expected profile, and flag the requesting device for troubleshooting based on a lack of correspondence between the retrieval profile and the expected profile. Additionally methods for discovering related devices, predicting that the related devices also require troubleshooting, and limiting restorative measures to only those devices that have been confirmed to be affected by a service issue may also be implemented by the system.