A change of a user device from a wireless connection to the enterprise network to a wired connection to the enterprise network (or a cellular network) is detected. In response, a snapshot of network conditions relevant to the user device are detected. A health check on the network conditions can identify specific network issues negatively affecting the user device and the issues are remediated. A remediation model is generated with AI that a different user change will occur based on a later health check revealing similar network conditions to the earlier health check. In response, the issues are automatically remediating the specific network issues based on the earlier stored remediation the earlier.