TCP 443 port shared OpenVPN with a website under Cloudflare



  • This is a somewhat specific issue that I haven't found much about online.
    I was experimenting with having a OpenVPN server on TCP port 443, however I also have a Nextcloud server on port 443, so I used OpenVPN port share function, but this breaks Cloudflare.
    Whenever I make OpenVPN the "proxy" for the website, I get error 525 - SSL handshake failed. So OpenVPN is doing something to the traffic to break SSL.

    Unfortunately I haven't been able to find any additional configuration directives for OpenVPN to fix this. I am hoping someone had previous experiences.
    Technically placing Cloudflare in flexible SSL mode would "fix" this, but then connections to my server would be in plain HTTP and that still has to traverse the Internet.


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