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@Nnnes: Thanks for sharing this.

This is not difficult to set up assuming you have already followed the instructions to set up SSH via cloudflared access ( and are able to SSH into the host.

In WinSCP's Advanced settings, go to Connection > Proxy. Set "Proxy type" to "Local". Under "Proxy settings" in "Local proxy command", copy and paste the same command that you have for your ProxyCommand in your SSH config file, e.g.
cloudflared access ssh --hostname

(don't include ProxyCommand at the beginning). You shouldn't need to change any other settings to make the tunnel work; just set up your authentication (username, password/SSH keys, etc.) as usual. I think the "Host name" field in the basic settings can be anything as long as it's not blank.

Re: Cloudflare Tunnel + WinSCP?

What is "Cloudflare tunnel"? Is it a proxy? What kind of proxy (HTTP, SOCKS, other?)? Or is it an SSH tunnel?

Cloudflare Tunnel + WinSCP?

Is there a tutorial how to connect through a Cloudflare tunnel?