RDWeb with Webclient disconnect when it tries to RDP

Thim 65 Reputation points
2026-07-03T01:42:46.19+00:00

I have a RDWeb with Webclient installed, it works fine when there is one single session host but when I try to add another one, I was able to RDP to the session host but when the session host tries to RDP to another server (in the collections), it logoff by itself. When I click on the RDP icon in the connections, it will RDP to the session host, then it will login to the desktop, then it will try to RDP to the server in the collection, no normal RDP popup, just blank screen and then it will logoff by itself. We are trying to put this RDWeb to the App Proxy so, this is the first time that we are doing this. Anyone have this experience are greatly appreciated.

Windows for business | Windows Server | User experience | Remote desktop services and terminal services
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  1. Xuan Nhu 330 Reputation points Independent Advisor
    2026-07-03T02:46:40.66+00:00

    Hi Thim, this looks more like RD Connection Broker redirection failing than a pure RD Web issue, because the single-host setup does not require the same redirected hop that appears once a second Session Host is added. Please check whether the RD Gateway RAP authorizes the actual redirected target for every Session Host in the collection, including the FQDNs and IPs that the broker/client may use, and review Applications and Services Logs\Microsoft\Windows\TerminalServices-Gateway\Operational plus Microsoft-Windows-TerminalServices-SessionBroker-Client/Operational during the failed attempt. For isolation, test the same collection internally through RD Web or the generated .rdp file while bypassing Microsoft Entra Application Proxy; if internal redirection works, the issue is likely in the App Proxy/RD Gateway publishing layer rather than the RDS collection. For Microsoft Entra Application Proxy, Microsoft requires RD Web and RD Gateway to be published as a single app with a common root, and for RD Web Client specifically the internal and external FQDN must match, otherwise WebSocket connection errors can occur. Also confirm the Application Proxy connector is version 1.5.1975 or later, disable HTTP/2 if the connector runs on Windows Server 2019, and set the RDS deployment RD Gateway server name to the published external URL with Password Authentication. If you can share the RD Gateway Operational log entry and confirm whether the issue reproduces internally without App Proxy, we can identify whether the failure is at RAP authorization, broker redirection, DNS/certificate resolution, or the App Proxy configuration.

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