For SCP, you need to specify ssh otherbox as a Shell on:
https://winscp.net/eng/docs/ui_login_scp

martin wrote:

What protocol do you want to use on the target server?

In general nothing has changed in recent versions of WinSCP in respect to this.

The server supports SCP. Can you test a similar setup on your end and let me know the results?

What protocol do you want to use on the target server?

In general nothing has changed in recent versions of WinSCP in respect to this.

My putty configuration connects to a host that serves as a gateway. I cannot use a tunnel in this environment. To access other server's the putty configuration's command execution is used to 'ssh otherbox'.

The putty shell ends up where it should. When I load this configuration in WinSCP it doesn't execute the command and always ends up on the gateway. I have gotten WinSCP to work as I want via the putty config in the past but cannot make it work in v5.7.1 (build 5235).

Is it possible to still do this and any suggestions for what to try next?

Thanks