After every Win10 feature update you may find that your PC(s) are no longer shown as online on the server dashboard and the client connector runs but doesn’t show as connected. If you try and re-run the connector from the server (https:\\<servername>\connect) the installer will often crash. If it completes and you are reconnected then all is good (until the next update), but it doesn’t work the simplest and quickest solution to get the workstation reconnected is as follows:
Uninstall the Client Connector for Windows Server Essentials
Delete all the Scheduled Tasks found under Microsoft\Windows\Windows Server Essentials
Delete the parent folder of those scheduled tasks (i.e. Windows Server Essentials)
Install the connector from the server (https:\\<servername>\connect)
Most of the time the PC won’t even need a reboot.