We are actually trying to simulate the Linux box as AppGW. During SSL negotiation , Client sends "Client Hello" and Server Responds with "Server Hello" with its Certificate to the Client. Document Details Azure Tip #9 Application Gateway Backend Certificate not whitelisted Error, Azure DevOps Fix for Access to path \SourceMapping.json is denied. One pool has 2 servers listed as unhealthy and the error message we see is below: "backend server certificate is not whitelisted with application gateway .Make sure that the certificate uploaded to the application gateway matches with the certificate configured in the backend servers. AppGW is a PaaS instance , by default you wont get access to the Applicaiton Gateway. Did the drapes in old theatres actually say "ASBESTOS" on them? In this article I am going to talk about one most common issue "backend certificate not whitelisted", If you check the backend health of the application gateway you will see the error like this "The root certificate of the server certificate used by the backend does not match the trusted root certificate added to the application gateway. OpenSSL s_client -connect 10.0.0.4:443 -servername www.example.com -showcerts. Check the document page that's provided in step 3a to learn more about how to create NSG rules. Was the error "exactly" the same before you explicitly added the exported root rather than relying on "Digicert" as known authority? From your TLS/SSL certificate, export the public key .cer file (not the private key). @einarasm read thru the responses from @krish-gh, specifically around leveraging OpenSSL toolkit to query the backend pool for the certificate trust chain, example: %> openssl s_client -connect 10.0.0.4:443 -servername www.example.com -showcerts. Now, this is the frustrating partwithin IIS, all of my sites are bound too each specified certificate (sharing a single cert across all the sites wont work for this scenario because of the difference in SSL and URL names), What the MSFT document (https://docs.microsoft.com/en-us/azure/application-gateway/application-gateway-end-to-end-ssl-powershell) fails to tell you, is that you need a Default SITE binding to a certificate, without SNI ticked. @JeromeVigne did you find a solution in your setup? Otherwise please share the message in that scenario without adding root explicitly.
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