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I'm having a strange problem with IIS 10 setup on a Windows server 2022. When accessing the site with http, it loads fine without issues. However, with https, I get a login prompt. Website has anonymous authentication enabled and all other authentications disabled. I thought maybe port 443 is going to a different site on the server so I stopped all other sites. I even tried switching this site's SSL to a self-signed certificate to confirm IIS is forwarding to correct site. I was able to confirm with browser giving certificate warning. When I ignore the warning and proceed, I get 401 NTLM login prompt. I tried entering a valid user credentials just to see but keep getting the prompt repeatedly.

I have similar setup on other servers and they work fine. Can't figure out why only https is asking for login credentials.

Any help is appreciated.

Bindings dialog Authentication dialog

Lex Li
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Venu Gopal
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  • Enable FRT to see which module gives you that 401, https://learn.microsoft.com/en-us/iis/troubleshoot/using-failed-request-tracing/troubleshoot-with-failed-request-tracing and that's the way to get started. – Lex Li Jan 26 '23 at 00:29

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