Hi Advait Mohammad,
Error 0x50331670 usually indicates that the connection attempt is being blocked before the session can even initialize, and since you’ve confirmed credentials are fine, the focus should shift to the contractor’s local environment. In many cases, restrictive outbound firewall rules or corporate group policies prevent RDP traffic from leaving the machine. If his company enforces outbound filtering, the RDP client may never reach your gateway.
One way to confirm this is to have the contractor run a simple telnet or PowerShell test to your RDP host on port 3389. If the connection fails immediately, that points to a local block. Another angle is to check whether his corporate VPN or endpoint security software is interfering, some vendors explicitly disable RDP connections for security reasons. If possible, ask him to test from a different network segment or temporarily bypass his corporate VPN to see if the behavior changes.
On your side, it’s worth confirming that your RDP gateway and firewall are allowing external connections and that no conditional access policies are rejecting his device. Since you were able to log in with his account locally, the account itself is not the issue. This really narrows it down to his client environment.
I hope the response provided some helpful insight. If it clarified the issue for you, please consider marking it as Accept Answer so others with the same issue can find the solution.
Jason.