Examples described herein include systems and methods for contextually providing automated device enrollment into a management system. A management application on a user device can receive network settings for connecting to a local server. The network settings can be preconfigured by an administrator. The management application can cause the user device to send an enrollment request and a device identifier to the local server. The device identifier can be used to validate the device and provide a security token to the management application. The management application can use the security token to complete enrollment of the user device.