I haven't quite worked out the rules yet but some GH pages allow full TLS on CF (but not strict cert validation obviously) and some require flexible. I think org pages need flexible (plain HTTP) but project ones support HTTPS (if on a subdomain)?
This update may change all that so will need to experiment again. If it does break things then any new sites after the 15th may not be able to be made to work. If using a CF page rule or HSTS headers to permanently redirect to HTTPS then this could be a problem.
https://support.cloudflare.com/hc/en-us/articles/200170416-W...
Maybe GH doesn't want the responsibility of hosting everyone's private keys.
> HTTPS is not supported for GitHub Pages using custom domains.
Not unsurprising, but unfortunate.
Do you have any idea how TLS actually works? If this worked out of the box for custom domains, then GitHub would need to be able to impersonate those domains.
At the very least you'd need a way to upload a private key/cert combo that they could server in response to an SNI request. Given the sheer number of sites that they host (every user effectively has a custom GitHub pages page) that's not really feasible though. Hence only support for *.github.io as that only requires a single wildcard cert.
If you redirect your domain to my webserver, I can get a certificate for it. E.g. from Let's Encrypt.
Wordpress.com uses that and offers SSL certificates to "million-plus"[0] blogs with custom domains. It's certainly doable at scale, although I totally understand it not having priority for GitHub (esp if it doesn't fit their current technical setup).
[0] https://en.blog.wordpress.com/2016/04/08/https-everywhere-en...