Hello @Kendal Friesen ,
Thanks for reaching out.
I understand that your corporate application integrated with Azure AD for SSO and works internally. Could you please confirm authentication protocol which is being used by your application (SAML or OIDC)? if its SAML then Azure AD Application Proxy has native support for SAML SSO.
Are you able to access published application externally using IDP initiated Sign-On follow by going the https://myapplications.microsoft.com/ (MyApps) portal and accessing it from there, does it work by any chance or getting similar error ? because through IDP initiated Sign-On flow no additional configuration is required regarding the Reply URLs by this way we can isolate the issue.
If failing only for an SP-initiated flow (whereas you directly access application URL which redirect user to identity provider for authentication) In this case make sure the back-end application specifies the correct Reply URL or Assertion Consumer Service URL for receiving the authentication token.
Because when the application accessed directly using the external URL in the browser (SP-initiated flow). In this case it's important that the SAML request (generated by the Service Provider) includes the Assertion Consumer Service URL (AssertionConsumerServiceURL), which matches the Reply URL of the published web app in the SAML SSO configuration.
so wondering If the Reply URL of the published app and the Azure AD Application Proxy is identical in your scenario? you must configure 2 Reply URLS.
Example:
https://testSAML.contoso.com/ - This is the External URL of the Azure AD Application Proxy app
https://testSAML.contoso.com/Saml/ - This is the Reply URL (Assertion Consumer Service URL) of the published app. (the SAML response will be posted to this endpoint). This must be the default one.
To view/ add / modify the reply URLs, go to the Azure Portal -> Azure Active Directory -> Enterprise Applications -> Locate the application
Note
- Use always identical internal & external URLs (see Custom domain configuration ) for the publishing, if it's possible (to avoid issues with hard coded internal links).
- If the internal and external URLs are different and the reply URL of the published app must be specified by the internal URL, in this case you must install the browser extension on the desktop clients and you must activate the Azure AD Application Proxy redirection for the Edge mobile browser on iOS/Android.
Hope this helps.
------
Please "Accept the answer" if the information helped you. This will help us and others in the community as well.