If you need an application on your Windows server to start automatically after the server reboots, the simplest way is to enable Autologon, a free tool by Microsoft.

Using Autologon

  1. Download https://docs.microsoft.com/en-us/sysinternals/downloads/autologon on your server (70KB)
  2. Extract the files and run the Autologon.exe tool. Accept the license agreement to continue
  3. Enter your 'Administrator' username and password and click Enable. You'll see an 'Autologon successfully configured' message. Click OK.
  4. Right-click the Start button and choose "Run". Type in:    shell:startup
  5. Click OK.
  6. This will display the startup folder (which is empty by default). You can drop a shortcut to your installed applications that you want to automatically start into the startup folder.

Now each time the server is rebooted, the Administrator account will automatically log in and start the applications you put shortcuts for in the startup folder. When you connect to the remote desktop, you'll see the applications running.

If you have a critical desktop application that you need to keep running, you might also consider a commercial solution such as AlwaysUp which can also restart applications on boot, or if they crash or close for any reason.