Need help with setting up a proxy

I need to be able to contact a server by going through my firewall. The situation is pretty much exactly as described on the Proxy page of the WinSCP manual. The problem I am having is, these instructions are not working for me. I am getting a time out when trying to use this.

Here is my question, short of someone taking the steps to talk me through every single configuration parameter I need to set... on the session screen, do I use the ultimate destination server name or the proxy server name for the hostname? What username and password do I enter here? Anything else that I must enter for it to work?

On the proxy screen, what parameters do I need to enter? How do I make sure that when the server I am contacting asks for a username and password that the correct information is being sent? Please help. I'm desperate to get this working.

RobertGonzalez wrote:

on the session screen, do I use the ultimate destination server name or the proxy server name for the hostname? What username and password do I enter here? Anything else that I must enter for it to work?

The ultimate destination server along with credentials for that server.

On the proxy screen, what parameters do I need to enter? How do I make sure that when the server I am contacting asks for a username and password that the correct information is being sent? Please help. I'm desperate to get this working.

There are boxes for the username and password on the proxy page.

The manual says:

Telnet/Local Proxy Command
If you are using the Telnet proxy type, the usual command required by the firewall's Telnet server is connect, followed by a host name and a port number. If your proxy needs a different command, you can enter an alternative here.
If you are using the Local proxy type, the local command to run is specified here.
In this string, you can use \n to represent a new-line, \r to represent a carriage return, \t to represent a tab character, and \x followed by two hex digits to represent any other character. \\ is used to encode the \ character itself.
Also, the special strings %host and %port will be replaced by the host name and port number you want to connect to. The strings %user and %pass will be replaced by the proxy username and password you specify. To get a literal % sign, enter %%.
If a Telnet proxy server prompts for a username and password before commands can be sent, you can use a command such as:

My normal process for SSH'ing into the machine is:
> telnet firewall, enter firewall username and password when required
> connect hostname, enter host machine username and password when required

If the manual is right, it looks like the connect command is going to be given the firewall username and password when I need to give it the host username and password. Or am I reading this wrong?

RobertGonzalez wrote:

My normal process for SSH'ing into the machine is:
> telnet firewal, enter firewall username and password when required
> connect hostname, enter host machine username and password when required

Where do you put your username and password? As part of the connect command or later?

Telnet to firewall process:

From there, SSH to the web machine:

This is the handshake that seems to be failing in WinSCP. I have been able to set this up properly in Hummingbird, but to be honest, Hummingbird is a piece of crap when it comes to file transfer in this way. Not to mention I really love the WinSCP interface so getting WinSCP to handle this would be a huge relief for me.

Have you tried
?

Yep. I still get a timeout notice.

RobertGonzalez wrote:

Yep. I still get a timeout notice.

Can you post a log file for that?