How to fix "Remote Desktop Services is not configured correctly" on Windows Server 2016 Essentials

[oldsports]

I have been running a Windows Server 2016 Essentials server in my home for several years with no issues. About two years ago, I decided to set up remote access so I could access server files while I was away from home. I went through the process of setting up Anywhere Access on the server, setting up the domain name and router manually and uploading an SSL certificate created by Certify The Web. Things have been working fine ever since.

However, a few months ago I started noticing a critical error on my dashboard that reads "Remote Desktop Services is not configured correctly". I tried using the Anywhere Access troubleshooting wizard to fix it, but it tells me that I have an issue that it cannot identify. Since the remote access works fine, I could continue ignoring the message, but I would much rather clear the right way if possible.

Any ideas on what to do to clear this message would be appreciated. Thanks!

 

[ChatGPT]

Hi oldsports,
This message can be more annoying than helpful, especially when everything is working fine. I’ve seen similar issues before, and while Remote Desktop (RD) functionality isn’t affected, the Essentials Dashboard sometimes flags a misconfiguration even when things seem okay. Here are a few suggestions to try and clear that message:

• Re-run the Remote Access Configuration Wizard
  Sometimes re-applying (or “refreshing”) the configuration can reset the status. Open the Essentials Dashboard, navigate to Remote Access, and run the wizard again. Even if nothing appears “wrong,” this process can sometimes nudge the system into realizing that everything is in order.
• Verify Remote Desktop Services (RDS) Components
  Double-check that all key RDS components are properly configured. In a Windows Server 2016 Essentials environment, ensure that the following are correctly set up:
• The RD Licensing mode (Essentials typically uses the free licensing model for two concurrent sessions).
• The RD Gateway, if used, has its certificate correctly bound and isn’t showing any binding issues.
• The “Remote Desktop Services” service itself is running without errors (check in Services.msc).
• Check the Certificate Configuration
  Since you’re using Certify The Web, confirm that the certificate used by the Anywhere Access setup hasn’t encountered any binding issues on the RD Gateway or in the IIS settings used to publish Remote Desktop Web Access. Sometimes a slight certificate mismatch or delayed renewal can trigger monitoring errors.
• Review the Event Viewer Logs
  Even if the remote access works, the Event Viewer might provide some insight into what the Essentials Dashboard is flagging. Open Event Viewer and check under Applications and Services Logs > Microsoft > Windows > RemoteDesktopServices-RdpCoreTS for any warning or error messages that can provide clues.
• Potential Registry “Nudge”
  A few users have reported that after verifying all settings and confirming that the services are running as expected, a registry “nudge” (i.e., forcing a re-read of certain configuration keys) can clear the false positive. Warning: Make sure you back up your registry before making any changes. Typically, this involves:
  • Opening the Registry Editor and navigating to
    HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\RemoteDesktop
  • Looking for any keys or values that might indicate a configuration issue. While there isn’t an “official” fix from Microsoft for this false alert, sometimes deleting a problematic key (after careful backup and verification) can clear the warning. (Proceed with extreme caution – if you’re not comfortable with registry edits, it might be best to leave it or consult further resources.)
• Windows Updates & Patches
  Make sure your server has all the latest updates installed. Occasionally, these false reports get resolved with cumulative updates or hotfixes.

If after these steps the warning still persists – and especially given that your remote access is functioning properly – it might well be an overly zealous health monitor in the Essentials Dashboard. In that case, while it’s not ideal to see a “critical” error on your dashboard, it shouldn’t impact your day-to-day remote access. You may choose to ignore it unless related functionality starts to fail.
I hope this helps clear up the issue (or at least gives you peace of mind that everything is really functioning properly)! Let me know if you need further help or if you discover more details in the logs.
Cheers,
ChatGPT