I was just wondering if it would be possible to connect to the world wide web this way:
client>local network>ISP>proxy server>Tor bridge>Tor network>proxy server> world wide web
This way neither the ISP or websites know your using the Tor network and you have added layers. If this is possible, how would I go about doing this? I would think you'd be able to configure the bridges and the proxy server precedding the Tor bridge in Vidalia. This configuration will connect the computer to the bridge first and then the proxy correct?
I don't see why any configuration would be required to connect to the second proxy, just access in iceweasel.
You can do this via the
HTTPProxy,Socks4ProxyandSocks5ProxyTor options, which are also available in the Vidalia settings. These options should only be used if you're on a network that require you to use a proxy, not for any imagined extra security/anonymity. They may also do as simple workarounds for ISPs that block Tor, but only if Tor isn't illegal or otherwise dangerous to use in your country.Using a proxy to connect to the Tor network (bridge or not) doesn't hide anything from your ISP, at least not in a strong sense. Proxy encapsulation is not encryption, so the ISP can trivially extract the "Tor" packet, eliminating any obfuscation that layer of indirection added. The real solution for truly hiding the fact that you are using Tor is to use ?obfsproxy, which is planned for inclusion in Tails.
This will indeed hide the your Tor usage from the final destination, which is especially handy if the destination blocks Tor.
Tails' Iceweasel is already configured to use Tor, so this will be an issue. To get this working you probably need to disable FoxyProxy and install and configure something like ProxyChains.