Re: How do I match this setup in WinSCP?
On the Login dialog, select "FTP" protocol. And I believe that the "SSL Direct" might be equivalent of "TLS/SSL Implicit Encryption" (if that does not work, try Explicit too). Change the default implicit port 990 to 6366 of your server.
And enter your hostname, username and password.
https://winscp.net/eng/docs/ui_login
And enter your hostname, username and password.
https://winscp.net/eng/docs/ui_login