Server 2022 not able to read file without extension

I moved my web server from server 2019 to 2022 and now certifytheweb is not longer working.
If I try to open a file without an extension I got an internal server error. If I remove the web.config file, I get an XML-processing error: syntax-error:


It is really strange, under 2019 was everything working fine.
I have currently no idea, why IIS is interpreting the file without an extension as an xml file and why the web.config file creates an internal server error?

Has anybody an idea what’s going wrong?

Certify The Web doesn’t normally need an IIS configuration (it has it’s own built in http challenge process) however if I check your site I see that your server is running Apache (not IIS). This means that the apache server will be using TCP port 80 and the default http challenge server will not be able to listen for http validation checks (which it can do if you are just using IIS).

Your test file is actually being served OK, it’s just that your default content type (in Apache) for extensionless files appears to be XML, so the browser struggles to interpret that.

Is it possible that your old site proxied requests to Apache via IIS?

To continue with apache, set the the website content root path in your managed certificate settings (Authorization > Site Root Directory ). The app will then create a /.well-known/acme-challenge/ folder under that path when your run a Test or request a certificate.

In front of the IIS Sophos UTM is running. That’s maybe what you see as Apache.


I figured out, that in another web.config file, there was <mimeMap fileExtension="." mimeType="text/xml" /> which created the problem, because the same file extension was defined in two different ways.
Sorry for the confusion!

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Great, glad you got it working.