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We have a web app in Azure that needs to call a site in our on-prem location, we have configured Azure Relay and it works fine for HTTP if we use HTTPS we get

Could not establish trust relationship for the SSL/TLS secure channel with authority Error Status 500 - Internal Server Error. URL

Does the web site on the internal site need to use a public cert rather than an internal one from our CA?

Garry_M
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  • Any update on this? I have a similar problem. I found that getting a cert from a valid CA made this work OK. – RizcoTech Aug 29 '18 at 14:39
  • How are the HTTPS senders addressing the relay cloud service? Are they trying to send to https://contoso.servicebus.windows.net or are you doing something like tweaking the HOSTS file to map yourapplication.domain.net to contoso.servicebus.windows.net? The certificate for the cloud service at contoso.servicebus.windows.net has a subject of "*.servicebus.windows.net". If HTTPS senders are expecting a different domain/subject name then SSL certificate validation will fail. – Dave Stucki Oct 20 '18 at 02:40

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