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ASP.NET with Windows authentication not working anymore

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In 2013, I built an ASP.NET Webforms intranet application with Windows authentication and everything worked fine.

FYI, back then, I was running Windows Server 2008. Now, I am running Windows Server 2019 which contains the domain user account.

Today, I cannot get it to work properly on my dev machine - not even a new simple dummy test site.

On my development PC, I am running Windows 10 Pro with the full IIS on it - I believe it is IIS 10.

So what's the problem?

On my development PC, when I launch default.aspx I get a login prompt dialog box rather than a seamless recognition of the user account (and I should not get a dialog box).

I get the same issue with:

Microsoft Internet Explorer v11
Microsoft Edge
Microsoft Edge Chromium


On IIS for the dummy test site, under Authentication I have:

Anonymous Disabled
ASP.NET Impersonation Enabled
Windows Authentication Enabled

On the ASP.NET Webforms site, in web.config at the root of the site I have:

<system.web><compilation targetFramework="4.5" debug="true"><assemblies><add assembly="System.Design, Version=4.0.0.0, Culture=neutral, PublicKeyToken=B03F5F7F11D50A3A" /><add assembly="System.Web.Extensions.Design, Version=4.0.0.0, Culture=neutral, PublicKeyToken=31BF3856AD364E35" /><add assembly="System.Windows.Forms, Version=4.0.0.0, Culture=neutral, PublicKeyToken=B77A5C561934E089" /><add assembly="System.DirectoryServices, Version=4.0.0.0, Culture=neutral, PublicKeyToken=B03F5F7F11D50A3A" /></assemblies></compilation><httpRuntime targetFramework="4.5" /><authentication mode="Windows" /><identity impersonate="true" userName="DOMAINNAME\AdminUser" password="pass" /></system.web><system.webServer><validation validateIntegratedModeConfiguration="false" /></system.webServer>

I have tried changing the targetFramework to 4.8 on the ASP.NET Webforms site but no difference.

I also tried binding a dedicated SSL certificate in case the authentication protocols between client and server has changed between IIS 7 and IIS 10 and Windows 2008 and Windows 2019.

Any ideas? Thanks.


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