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RDS Connection Issue

Josh Adcock 0 Reputation points
2024-06-19T16:08:15.4833333+00:00

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.

Windows Server
Windows Server
A family of Microsoft server operating systems that support enterprise-level management, data storage, applications, and communications.
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Remote Desktop
Remote Desktop
A Microsoft app that connects remotely to computers and to virtual apps and desktops.
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  1. Karlie Weng 15,916 Reputation points Microsoft Vendor
    2024-06-20T02:38:38.66+00:00

    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?

    User's image

    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

    User's image

    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

    Additional resources:

    If the Answer is helpful, please click "Accept Answer" and upvote it.