Methods, apparatuses, and systems directed to facilitating troubleshooting wireless connectivity issues in a wireless network. In accordance with one embodiment of the present invention, either a diagnostic supplicant in the wireless client or a diagnostic manager initiates a troubleshooting protocol between the diagnostic supplicant and the diagnostic manager over a diagnostic link in response to one or more events. In one embodiment, after the diagnostic supplicant establishes a link to a diagnostic manager via a diagnostic link, the diagnostic supplicant generates and transmits a problem report to the diagnostic manager. The problem report initiates a troubleshooting protocol between the diagnostic manager and the diagnostic supplicant.