TOR, PuTTY, Privoxy and HTTP/S question

Hello,

I use TOR/Privoxy/FireFox and I want to add a SSH server via. PuTTY.

I think I have things setup correctly but I can't find *any* "how-to"
for TORifying PuTTY.

Please read over my setup as I have posted it below and tell me if I
missed something or set something incorrectly (ex. Socks4 not Socks5).

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1. Anyone know how to use Tor, Privoxy, FireFox and PuTTY in conjunction?

2. I want to use SSH and port forward (port 22) my Tor connetion; is this
possible?

3. What type of tests should I perform on my connetion to insure SSH
port forwarding and Tor are working correctly?
(For example: IPtests, Environemnt tests, TraceRoute, etc, etc?)
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My setup:

1. FireFox: set to "127.0.0.1:8118"

2. Prioxy: set to "forward-socks4a / 127.0.0.1:9050 ."

3. TOR: setup defualt

4. PuTTY:
A. Session:
> Host Name > "My SSH Sever's Name"
> Protocol > Proxy > Proxy Type > "Socks 5"
> Proxy Host Name > "127.0.0.1:9050"
> Proxy Host Name > Do DNS name lookup at proxy end > "Yes"

B. SSH:
> Encryption Cipher Selection Policy > "Blowfish/AES/3DES/--Warn Below Here--/DES"

C. SSH > Tunnels:
> Port Fowarding > Local Port Accept Connection From Other Ports > "cheked"
> Add New Forward Port > Source Port > "127.0.0.1:9050" > "ADD"
> Destination > "Dynamic"

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If I am correct this will make my intenet connection (HTTP, HTTPS, FTP,
etc.) follow this route:

FireFox > Privoxy > TOR > PuTTY(SSH Server) > Net

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BTW, I was thinking of "chaining" 2 or 3 SSH Servers together...what do
you think?

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Thank you very much

 

Why would you wish to chain SSH with Tor? If anonymous browsing is your goal, you would be compromising this by tying yourself to a single server at the end. All an attacker needs to do then is observe the unencrypted traffic exiting this server - if you are the only user (or one of a few) using this server then identifying which traffic is yours becomes trivial.

On the other hand, if you need to use SSH to access a specific server and you wish to do this via Tor then you need a SOCKS client like SocksCap or FreeCap to "Socksify" PuTTY (forward its traffic via SOCKS). Privoxy performs this function for web browsers only. For more information see the JAP,TOR,Socks proxy ,tunneling and Stunnel thread (just substitute Proxomitron with PuTTY here).

While it is possible to chain SSH servers together, all you will end up doing is creating a lower-security version of Tor (since you are using the same path all the time while with Tor the path used changes regularly and is shared with other users).