LetsEncrypt Certificates for Development Machine

I'm fairly new to testing Lets Encrypt and I have some Windows Server 2016 machines that I'd like to test on.

When I attempt to setup Lets Encrypt certs, I, for the most part get the same error. Essentially that the sites needs to be publicly accessible.

Certify The Web:
"Config checks failed to verify http://SITE.com is both publicly accessible and can serve extensionless files e.g. http://SITE.com/.well-known/acme-challenge/configcheck"

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Win.Acme v1.9.10.1:
"Authorization result: invalid
 [EROR] ACME server reported:
 [EROR] [type] urn:acme:error:unauthorized
 [EROR] [detail] Invalid response from http://SITE.com/.well-known/acme-challenge/Z7oLhYqhHZ6gFO6C9LVTVG8h60AcAP_BLYWDvWKzsws: "<!DOCTYPE HTML PUBLIC "-//IETF//DTD HTML 2.0//EN">
<title>500 Internal Server Error</title>
 [EROR] [status] 403"

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Is it possible to get Lets Encrypt certificates to work in a Development/Test environment? Perhaps I'm missing something obvious, like a work-around putting in files in Production. (Unfortunately, that sorts defeats the security aspect of it.)

Any advice would be appreciated.

Thanks for your assistance.
TessandoIT AdministratorAsked:
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nociSoftware EngineerCommented:
LetsEncrypt has no idea if a system is sued for production, testing or development.., that's you who decide what to use your systems for.

The error message show "unauthorized" / not publlicly accessible......
You system MUST be reachable for the LE servers (they try to fetch some data from there)...
 The query fails ==> you don't get access.

LE will never tesolve .local addresses as they cannot be reached from the internet as a domain name.

Another option might be DNS authorisation during setup. You need to be able to update DNS then.
Either manual (which doesn't scale well) or through a DNS Plugin...  LetsEncrypt 0.20+   has those options as plugins.

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Windows Server 2016

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