RDP Connection Issues on Windows Server 2022

Hi Gabriel,

I hope you are having a nice day.

Below are several troubleshooting steps you might try. Hopefully, it could help you solve the issue.

I) Recreate and Bind the Certificate

• Open Certificates (Local Computer) -> Remote Desktop -> Certificates
• Delete any existing certificate, then right-click -> Create Self-Signed Certificate
• In Registry (under …\RDP-Tcp\SSLCertificateSHA1Hash) ensure the thumbprint matches your new certificate.
• Restart Remote Desktop Services

II) Temporarily Disable Network Level Authentication

• Run gpedit.msc -> Computer Config -> Admin Templates -> RDS -> Security
• Set “Require user authentication for remote connections by using Network Level Authentication” to Disabled
• Restart the server or run gpupdate /force

IV) Verify FIPS/Encryption Settings

• Open secpol.msc -> Local Policies -> Security Options
• Locate “System cryptography: Use FIPS compliant algorithms…” and set it to Disabled
• Reboot if you make a change.

V) Check Windows Firewall & Port Binding

• Confirm TCP 3389 is allowed in Windows Defender Firewall
• Run on the server: netstat -ano | find ":3389". (Ensure the listening PID is TermService and nothing else is bound)

VI) Review Event Logs for Clues

• In Event Viewer, look under:
  • Applications and Services Logs -> Microsoft -> Windows -> RemoteDesktopServices-RdpCoreTS
  • … -> Windows -> TerminalServices-LocalSessionManager
• Even non-critical warnings there can hint at driver or security-layer failures

Give these a try and let me know which steps make a difference. If none of the above resolve it, we can dig deeper into RDS licensing, advanced TLS settings, or even reinstall the RDS role as a last resort.

Hope one of these gets you back in!

Best regards,

Finn Dang