Windows Update 1903 and Windows Server Connection Issues

One of my clients has a small network consisting of 12 Windows 10 PCs and a Window Server 2016 Essentials server. As Microsoft is notorious for, not all of the computers on the network received Windows Update 1903 at the same time. One afternoon, the client called me and told me one of their computers kept restarting and downloading an update. By the time I got to the location, the update had finished installing and the Windows 10 PC was on Windows version 1903. But there was a problem, the computer was no longer on the network.

The Windows Server 2016 Essentials dashboard showed the device as still being connected, but on the PC itself, we were not able to access the server in almost any way. I could not even remote desktop via the server IP (which I am normally able to do.) Fortunately, I was able to download the connector software. But getting the PC back on the Windows Server after the 1903 update was fairly challenging. Fortunately for you, I am going to break it all down.

I can save you a lot of time in this paragraph. You can avoid any headaches with the Windows Update 1903 if you just download the Windows Update Assistant tool from the Microsoft website. When I used the Update Assist on every other computer on the network, I had no problems at all. The 1903 Update downloaded (100mb connection) and installed in about an hour. After installation and a single restart, the Windows PC retained all of its connection information to the Windows Server 2016 Essentials server. If you have not made the jump to Windows Update 1903, please save yourself some time and download the Windows Update Assistant. If its too late, and Windows Update has already installed your Windows Update 1903, then read on because I have been there, and I can help.

EDIT: Some people might experience an issue where their Windows client is not showing up on the Windows Server Essentials dashboard. I explain how to fix that problem in part 2.

If Window 10 automatically installs the Windows Update 1903, you won't be able to use the Windows Update Assistant. Every Windows computer that I have encountered that automatically installed Windows Update 1903 was no longer able to access its Windows Server Essetnials host. The first thing you're going to need to do is uninstall the Client Connector for Windows Server Essentials.

1. Press the Windows key and type Add Remove Programs. That will take you to a list of installed programs.
2. Find Client Connector for Windows Server Essentials and uninstall it.

Once you've uninstalled the Client Connector, you will need to remove the client from the domain. You will not be able to rejoin the network until you have left the domain.

1. Press the Windows key and type Control Panel.
2. Open the Control Panel and click on System and Security.
3. Click on System.
4. Click on Change Settings.

This will open up the System Properties screen. Here you can rename the computer (not needed for what we are doing here) and change the domain your Windows computer is connected to. Make sure the System Properties screen is on the Computer Name tab.

1. Click Change to open the Computer Name/Domain screen.
2. Remove the Windows client from its current domain by clicking the Workgroup option.
3. Name the Workgroup whatever you want and click okay.
4. Restart your computer.

Once you resart the computer, you will be able to download the connector software again and rejoin the domain. You might also want to remove the device from the devices list of the Windows Server Essentials dashboard, but I did not find that to be a neccessary step. Just follow the connector software wizard instructions and you should be back on the network shortly.

There are a few other problems I've found over the last few days. Part two of this post goes into more ways to solve your connection problems.