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I'm not familiar enough with Cloudflare's error messages
or deployment with Cloudflare
to know what exact behavior that corresponds to, but I'd guess that most likely it can open a TCP connection to port 443 on what it thinks is your server, but it's not getting HTTPS on that port or your server isn't configured to serve up the right certificate for that hostname or the web server software running on it is otherwise broken. Might be some sort of intervening firewall.
I don't know where your actual server is, may not even be accessible to me. But if you have a Linux machine that can talk to it directly -- including, perhaps, the server itself -- you should be able to see what certificate it's handing back via:
That'll try to establish a TLS connection, will send the specified server name so that if you're using vhosting on the server, it knows which site to return, and then will tell you what certificate the web server used. Would probably be my first diagnostic step if I thought that there was a problem with the TLS handshake on a machine I was running.
That might provide enough information to you to let you resolve the issue yourself.
Beyond that, trying to provide much more information probably isn't possible without more information about how your server is set up and what actually is working. You can censor IP addresses if you want to keep that private.