Certbot issues on Windows IIS - Not going well

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Welcome to the Let's Encrypt Community, Tarjei :slightly_smiling_face:

IIS seems to have trouble serving extensionless files by default. Try creating a file named web.config in the acme-challenge folder with the following contents:

<?xml version="1.0" encoding="UTF-8"?> 
<configuration>
    <system.webServer>
        <staticContent>
            <mimeMap fileExtension=".*" mimeType="text/plain" />
        </staticContent>
    </system.webServer>
</configuration>

Then create a file named test in the acme-challenge folder containing "1234". If you can retrieve that file with your browser, try certbot again.

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