Devolutions Server & Gateway side-by-side via Azure Application Proxy

Hello Everyone!

I wonder if someone could help, or has come across this issue before. We are currently evaluating the Devolutions Team Starter Pack and trying to get Gateway to work with Devolutions Server via an Azure/Entra Reverse Proxy/ Application Proxy.

Current Setup:

We have a Windows 2025 server installed on prem running Devolutions Server with a side-by-side installation of Gateway server. We have existing Azure connectors on the LAN for other applications, so we have created a Enterprise Application in Azure to access the Devolutions Server via web and RDM with MFA SSO Enabled. This is all working fine and we can access our estate on RDM and Devolutions server using this setup.

Issue:

When trying to configure the Gateway server using the same reverse Proxy address within Devolutions server, it fails on the ping test and therfore marks it as "down". If we specify the internal address for the Gateway server it finds it and works without issue, however when connecting to sessions via the Gateway server, this only works when on the internal network, externally it fails (even though if we go into a RDP entry within the vault and test the Gateway connection, it passes)

Reading the forum post here (Best practices for Devolutions Server & Gateway deployment) it sounds like the Gateway server should be accessible via the same URL as the Devolutions server because the IIS handles the redirects. Has anyone got this to work using the same entra reverse proxy address?

Thanks!

Dave