The disclosed embodiments relate to approaches for diagnosing and resolving wireless network connectivity issues on an electronic device. The system includes a tool for automatically diagnosing and resolving wireless network connectivity issues on the electronic device. The tool may monitor and manage the wireless network connection on the electronic device. If a lack of wireless network connectivity is detected on the electronic device, the tool may run a series of test cases associated with wireless network connectivity issues on the electronic device. The tool may then notify the user of the results of the test cases, provide recommendations associated with the results to the user, and/or log data associated with the test cases.