Hello @Sivasubramaniam Sivakumar ,
Thanks for your time and patience. I was able to test this through in my lab. Here are the possible scenarios I tested.
- The Azure application proxy could not bypass the error caused due to invalid SSL certificate bound to the application. Any communication happening via port 443 (due to SSL binding), regardless of happening with or without AAD proxy in place. To find if the issues is due to SSL or application proxy, please validate the azure application proxy connector logs.
- The error message you shared seems to be a generic one which could be seen when Azure AD app proxy is not configured, connector is not updated, service is not running or the AAD application proxy connector server is not running.
For details on this please try the following:
- Configure the web application without IIS binding i.e. port 80
- See if the application is accessible without any issues on private network.
- Restart the IIS server and try to access the application proxy URL. If the issue persist then kindly validate the azure ad application proxy connector logs from the server. https://learn.microsoft.com/en-us/azure/active-directory/app-proxy/application-proxy-troubleshoot
Please do let me know if you have any further queries.
Thanks,
Akshay Kaushik
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