Disclosed are various examples for securing enterprise resources using a virtual private network. A client device can send a first unique device identifier for the client device to a remote management service upon enrollment. When a virtual private network application is first executed, the client device can send a second unique device identifier to the remote management service, where the remote management service is configured to store the second unique device identifier in association with the first unique universal identifier. During subsequent executions of the virtual private network application, the virtual private network service can authenticate the client device by comparing the first unique device identifier and the second unique device identifier to a device identifier received from the remote management service. A machine learning routine can be employed to identify anomalies as the virtual private network application is executed.