This affects iOS devices in deployments where devices are enrolled through the web, and then the iOS AirWatch Agent is pushed down to devices. Sometimes, when the Agent is initially opened on newly enrolled devices, it does not properly connect to the Console and will prompt the user to enroll again.
This issue does not occur if users enroll directly through the iOS AirWatch Agent.
This issue has been given identifier IAGNT-168438. This issue has been resolved in iOS Agent 5.1.