Techniques described herein relate to performing wireless diagnostic analyses including execution and evaluations of interactive content resources executed by execution devices on and/or for separate content receiver devices. A multi-phrase diagnostic session may proceed with an execution of an initial set of diagnostic modules on an execution device, during which interactive content is transmitted/received from a connected receiver device. The results of the diagnostic modules may be evaluated in real-time and transmitted to a diagnostic analyzer server to select additional diagnostic modules for execution during the diagnostic session. The diagnostic analyzer server may select the additional diagnostic modules based on based on response data received via the content execution device to the interactive content of the previously executed diagnostic modules, and/or data received from additional data sources related to the content receiver.