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windowsRDP: This problem can occur if the remote PC is running a version of Windows that is not configured

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This problem can occur if the remote PC is running a version of Windows that is not configured to support server authentication.

That message usually means the remote computer can’t complete the security handshake required by the client that’s trying to connect (most commonly with Remote Desktop / RDP).

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What it means (plain English)

Your local PC is trying to connect using modern, secure authentication (Network Level Authentication / CredSSP / TLS), but the remote PC is too old or misconfigured to support it.

This often happens when:

  • The remote PC is running an older version of Windows

  • Remote Desktop is enabled, but Network Level Authentication (NLA) isn’t supported or is disabled

  • The remote system hasn’t been updated with required security patches

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Common scenarios

  • Connecting from Windows 10/11 → Windows XP, Vista, or very old Windows 7

  • Connecting to a legacy server that hasn’t been updated

  • Using a third-party RDP client with stricter security defaults

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Ways to fix it (choose what applies)

✅ Option 1: Enable modern authentication on the remote PC (best)

On the remote computer:

  1. Open System Properties

  2. Go to Remote

  3. Check “Allow connections only from computers running Remote Desktop with Network Level Authentication”

  4. Apply and reboot

(Only works if the OS supports NLA.)

⚠️ Option 2: Lower security on the client (temporary workaround)

On the client PC:

  1. Open Remote Desktop Connection

  2. Click Show Options → Advanced

  3. Under Connect from anywhere, set security to RDP Security Layer (if available)

Or via Group Policy:

  • Computer Configuration → Administrative Templates → Windows Components → Remote Desktop Services → Remote Desktop Session Host → Security

  • Set “Require use of specific security layer” to RDP

⚠️ This reduces security and should only be used on trusted networks.

🔄 Option 3: Update the remote system

  • Install Windows Updates on the remote PC

  • Old Windows versions often lack required authentication support until patched

🧓 Option 4: Use a compatible OS

If the remote PC is running something like Windows XP or unpatched Vista, modern Windows versions may simply refuse to connect securely. In that case:

  • Upgrade the OS, or

  • Use a legacy RDP client in a controlled environment

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