Cloudflare SSL not being passed down with Windows AD

I self host local websites that are externally viewable. This is an issue I have had from day one and I normally disregard it. I have a local Active Directory that has a zone for the domain that I use externally. These records only get hit internally for lets say I set up a webserver and I go and add it to my zone so that it lines up with what domain you would use externally as well as internally (eg IIS01.mydomain.xyz = 10.0.0.50 internally, IIS01.mydomain.xyz = 1.1.1.1 externally) I can when I am not connected to my network access those sites and have full HTTPS capabilities but when I do it internally I get hit with err_cert_authority_invalid unless I import the root cert file that cloudflare provides. Is it possible to completely mitigate that and have HTTPS work as intended? I think it has something to do with the DNS zone I have I am just not sure how else to route my sites internally without it

It sounds like you have a few choices:

  1. Import that root cert
  2. Generate Let’s Encrypt certificates
  3. Find a way to use External DNS for those hostnames (I know just about zero about AD).

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