Lets Encrypt Web.config IIS Redirect for HTTP to HTTPs Allowing HTTP access to the .well-known Folder

Let's Encrypt offers a neat service providing free SSL certificates which can be renewed through a service. However, the renewal process itself can be tricky : it requires the Let's Encrypt servers to access to your server's filesystem along a non-HTTPs connection. This may sound simple, until you consider that you may also want to have a generic redirect from all other non-HTTPs requests to their HTTPs equivalent.

So how do you include the best type of 301 redirect, while also separately allow through any requests to the required to the ./well-known folder and all of it's sub-folders? Luckily redirects are infinitely configurable in IIS, and below are some of the ways we have achieved this using Web.config redirects:

          <rule name="Allow LetsEncrypt" patternSyntax="Wildcard" stopProcessing="true">
                    <match url=".well-known/*" />
                    <action type="None" />
          <rule name="Redirect HTTP to HTTPS" patternSyntax="Wildcard" stopProcessing="true">
                    <match url="*" ignoreCase="false" />
                              <add input="{HTTPS}" pattern="off" />
          <action type="Redirect" url="https://{HTTP_HOST}{REQUEST_URI}" />

This is specified as two rules, the first saying to 'take no action' for any requests that includes .well-known/<anything>, thereby causing IIS to ignore the second rule which says "redirect all requests that are not HTTPs to the corresponding HTTPs equivalent. So accessing will automatically redirect (with a 301 to  unless the .well-known pattern is found at the start of the request.


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