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The proxy is the most likely reason. From here, public DNS for both names returns Cloudflare's addresses, not GitHub's:

www.justinjindustries.com  A     104.21.20.72, 172.67.191.223
justinjindustries.com      A     172.67.191.223, 104.21.20.72
(+ Cloudflare AAAA, no CAA)

GitHub gets the certificate from Let's Encrypt, and Let's Encrypt checks the domain with an HTTP request to http://www.justinjindustries.com/.well-known/acme-challenge/... on port 80. With orange-cloud records that request goes to Cloudflare first. You noted that automated requests get Cloudflare challenges, and the validator is exactly that kind of request, so it never gets the token from Pages and issuance fails. The d…

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@rjsgud49
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