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Hi @User9183
Based on your description, I understand that you are deploying pure On-Premises Modern Authentication for Exchange Server 2019 CU15 with a local ADFS server (completely bypassing Office 365/Entra ID). The core issue is that domain-joined machines fail during the Outlook startup process with the error "There is a problem with your account," while non-domain machines work perfectly, prompting the user with the ADFS login page and successfully establishing a connection using a "Bearer" token.
The specific error 0xCAA9001F (Integrated Windows Authentication is supported only in the federation flow) typically indicates that Windows is attempting Integrated Windows Authentication (IWA) against Microsoft Entra ID (Azure AD), but the domain is not configured for cloud federation.
Since your environment is strictly on-premises, seeing a request directed toward https://login.microsoftonline.com/organizations suggests that the Windows Web Account Manager (WAM) / AAD Broker Plugin is intercepting the request on domain-joined machines before Outlook can execute the expected local ADFS OAuth flow.
Why the non-domain machines work:
- They do not attempt silent Integrated Windows Authentication.
- Outlook immediately falls back to prompting the user, successfully rendering the local ADFS login page.
- ADFS issues the OAuth token, Exchange accepts it, and Outlook connects via "Bearer." This proves your core Exchange OAuth configuration is working.
Please check the following configurations:
-Verify ADFS Global Authentication Policy
Integrated Windows Authentication behavior inside the corporate network can sometimes conflict with what WAM expects during on-premises modern auth. Please run the following command on your ADFS server:
Get-AdfsGlobalAuthenticationPolicy
Compare your results with Microsoft's recommended configuration for pure on-premises modern auth. In many hybrid/on-prem modern auth scenarios, ensuring FormsAuthentication is enabled for both Intranet and Extranet helps bypass silent IWA failures that trigger the AAD broker.
-Verify Outlook Build and Windows Updates
According to Microsoft documentation for on-premises modern authentication, Outlook requires a specific supported build version to natively handle the ADFS OAuth flow without trying to route through Entra ID. Please verify that your test clients are running a supported version of Outlook. Ensure the clients have installed KB5023706 (or newer cumulative updates). This update includes critical fixes for how the Windows Web Account Manager interacts with non-cloud endpoints.
-Registry Check for MAPI/HTTP and Exchange Modern Auth
Even though you mentioned registry settings are applied, ensure that DisableADALatopWAMOverride or EnableADAL are not inadvertently forcing cloud lookups. For Outlook 2016/2019/365 Apps connecting to on-prem Exchange via ADFS, ensure that MAPI/HTTP is explicitly enabled and that Outlook is explicitly told to look for your internal endpoint.
Please check these items and let me know the results of the Get-AdfsGlobalAuthenticationPolicy command so we can dig deeper.
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