Techniques are described herein for collecting and utilizing diagnostic information for advanced monitoring of wireless power delivery systems. Wireless power transmission systems and/or cloud processing systems accumulate significant volumes of data related to wireless devices, usage patterns, power delivery efficiency and system components. This data can be utilized to generate efficient and sophisticated power transmission schedules. Additionally, as discussed herein, the diagnostic information can be leveraged for advanced system diagnostics and health monitoring. Among other features, the diagnostic and health monitoring system can detect patterns and correlate events that lead to system errors or failures. In some embodiments, the diagnostic and health monitoring system can also provide error notification and/or automatic error correction.