Hello @Todd Wolfe ,
Thank you for reaching out Microsoft Q&A.
I understand that you have two separate login entries to set up SSO for an application using M365 SAML, with two specific reply URLs: one designated for managers and the other for staff. However, you have only a single User Access URL to initiate authentication.
In your scenario, if you configure the enterprise application with the Reply URL specifically designated for managers, the authentication token (SAML response) will only be sent to that configured URL within the application. Similarly, if you configure the application to use the Reply URL for staff, the SAML response will only be directed to the staff-specific URL.
This setup implies that the application can only support a single Assertion Consumer Service (ACS) URL at a time, meaning you cannot configure multiple Reply URLs within the same application instance to receive authentication tokens for different user groups simultaneously. As a result, it’s not feasible to authenticate both managers and staff using just one User Access URL for the login process. Each group would need to initiate authentication through a separate path, or you’d need to choose one Reply URL to handle authentication requests.
For more information, you can refer to this thread: Microsoft Q&A on Multiple SAML Responses.
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Regards,
Goutam Pratti.