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System.Net.Http.WinHttpException (80072F8F, 12175): Error 12175 calling WINHTTP_CALLBACK_STATUS_REQUEST_ERROR #2527

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It might be that the trust chain is ok but it's failing to negotiate a common TLS level and cipher suite, if you use IIS Crypto to check your enabled cipher suites and compare the working machine to the non-working machine you may find you need to enable some of the more modern suites like ECDSA ones.

If you don't share a matching set of ciphers between your machine and the acme-dns server then you can't connect. In particular if your 2012 server was an upgrade from Server 2008 a bunch of stuff doesn't work by default, 2012 is also past it's supported end of life but I'm sure you know that.

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@TorpedoCXC
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