2 servers, 1 IP/domain, running on a different port

I'm a bit confused on what to do here. I have 2 separate server machines both using the same IP address. I registered a free domain for it. The machine I want to use Lets Encrypt on is running on domain.com:81, which redirects using my router to port 80 on the server. If you go to domain.com:80 then it goes to the other machine which I don't control. My server is running Apache on Windows 10 while the server I don't control is running Windows Server IIS.

I haven't tried to run the Win-ACME fully yet, but I think that Let's Encrypt will check domain.com:80 and there is no way for it to check domain.com:81 (which redirects to port 80 on my server). So what do I do here? Can I do anything?

Hi @NotRealITguy

please read the basics:

Then you know: You can use dns validation:

Ok, I can't create a TXT record at _acme-challenge.domain.com because it's a free domain on https://freedns.afraid.org/ it says Creation of records beginning with _ are presently restricted to the domain owner only by default - this is temporary (2016-02-10)

Then you have to change your setup so you can use http validation via port 80.

Or you have to use another dns provider without that limit.

Sometimes free is expensive.

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