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iiswindows-server-2019

IIS Websites requested through HTTPS keeps showing a prompt for sign in instead of loading the site


I'm facing an issue with websites hosted on my server, if the request is made with HTTP (80) it will access the site without problem, but if I try to use HTTPS (443) the website shows a prompt asking for sign in credentials, the website doesn't work with Windows Authentication. So far I have checked that I have Anonymous Authentication enabled but can't seem to find what the problem is when requesting through HTTPS so the site loads and no message prompt is shown. The server is running Windows Server 2019.

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EDIT ON FEBRUARY 2024

I forgot about this question, however an important detail I didn't add here was that I was using the Centralized Certificates IIS addon as well as the AutoACME software for managing the SSL Certificates, adding the resolution below.


Solution

  • Something I didn't consider at the time of writing this question was that I was using the Centralized Certificates IIS addon on my particular case, so what generated the issue was that the Windows User's credentials changed and I didn't update them on the Centralized Certificates settings. Since the addon couldn't access the path where the certificate files where located because the user credentials were invalid, it showed that prompt.

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    I was using AutoACME for generating SSL certificates from Let's Encrypt CA, and even though they mention this issue on the AutoACME Wiki page I completely missed it.

    Even if you don't use the same tools on your Windows Server if the IIS user doesn't have read permissions for the folder where your PFX or certificate files are located this prompt will appear, so confirm that the folder hasn't been moved or lost the read properties. This behaviour can be triggered also if you are using Reverse Proxy or Url Rewrites to redirect requests to the https paths.