RDS Connection Issue

Question

I am setting up a new Windows Server 2022 Standard with two virtual machines, one as a database server, the other as an RDGateway / Terminal server. However, every time I try to connect to the RDGateway from an outside machine, I get the error message: "Your Computer Cannot Connect to the Remote Computer Because the Remote Desktop Gateway Server Address Requested and the Certificate Subject Name Do Not Match". I have followed several recommendations, such as binding the SSL certificate to the RDGateway, creating a self-signed SSL certificate, and verifying that the SSL certificate being handed out via IIS is the correct one, but still get the SSL mismatch. What am I missing? Any assistance would be appreciated.

Answer

Hello Josh Adcock,

Identify Remote Desktop Gateway server address and DNS name(s) the certificate secures: Click View Certificate -> Details -> Subject Alternative Name

Does certificate list DNS name that secures Remote Desktop Gateway server address?

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Possible Solutions:

When incorrect RD Gateway server address was entered in RDP client:

Update RDP client connection to use server name that is secured by certificate, RDP client -> Advanced Tab -> click Settings under Connect from anywhere -> Use these RD Gateway server settings

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Installed RD Gateway certificate does not secure RD Gateway server address:

Update RD Gateway certificate to use desired

RD Gateway Manager snap-in -> SSL Certificate tab -> Import a certificate into Personal Store -> Browse and Import Certificate

Note: If certificate does not show in list you must first import certificate .PFX into local computer

store.

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Note: Also see domain - Name Mismatch - Incorrect Remote Computer Name - Server Fault because certificate must secure Remote Computer and RD Gateway

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RDS Connection Issue

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