Please read FAQ. If that does not help, come back.

The current version of WinSCP can only ssh into one remote IP address. But as jump boxes are becoming the norm for firewall protection WInSCP can't be used beyond the jump box. It would be a great enhancement if the user was allowed to set up a chain of IP/hosts that would have to logged into before reaching the final host box. I don't know if this can be done or not but manually logging in and scping files down or up the chain of host boxes is a pain and takes forever. I have asked the administrators about other products but they have not heard of any tool that does this at this time. I think if you could do it, it would be a big selling point.