Google Talk in iChat behind a firewall

Note : this is an updated and (somewhat) tightened version of this hint at macosxhints for my personal reference. If it helps someone, great.

At work my computer is blocked from the outside world by a proxy. Here are the steps required to make iChat (Leopard) able to connect to Google Talk anyway.

1. Download the last version of proxytunnel. Version 1.8.0 compiles out of the box on Leopard, as long as you have the developer tools installed. Copy the proxytunnel binary somewhere nice, like /usr/local/bin.

2. In a terminal window, run

sudo /usr/local/bin/proxytunnel -a 5223 -p -d

(of course, replace by the actual URL or IP address of your proxy server)

3. In iChat Leopard, configure your google chat account as follows : server = localhost, port = 5223, Use SSL = yes, everything else ticked off.

After doing this, iChat should connect to your Google Talk account, and away you chat. If you are on a laptop, you’ll have to revert the iChat server setting to the regular when you leave the proxy jail, and change it back every time you come back to work (I guess proxytunnel can be left running without problems).

The original hint suggests a setup which takes care of doing all the heavy lifting through a customized /etc/hosts and Applescripts  — they works pretty well as-is, although 1) the proxytunnel syntax will have to be updated to look like what’s above when using 1.8.0 and 2) there’s no need to call “nslookupd –flushcache” on Leopard AFAICS.

After all these efforts, 2 nice bonuses to reach chat nirvana : 1) Chax will give you a nice unified contact list and Growl notifications in iChat, 2) How to chat with MSN, Yahoo and other contacts through Google Talk.

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13 Responses to Google Talk in iChat behind a firewall

  1. Bob says:

    I get: “iChat can’t verify the identity of “localhost.” An SSL error has occurred and a secure conection to the server cannot be made. What’s wrong?

  2. Primalmotion says:

    I’ve got the same problem than Bob. Any solution ?

  3. Matt G says:

    The SSL error is because the far-side site says “Google” but you are connecting to “localhost” which is a mis-match. You can safely ignore this error and then it will work. At least I was able to ignore the error and make use of it.

  4. Jon J says:

    Hmm, I don’t know how to compile proxytunnel. Is there a tutorial for such things? Thanks.

    • Andrew says:

      Install homebrew and run “brew install proxytunnel”. I find that is the easiest way to install *nix apps on mac.

  5. aidan says:

    yeah, i don’t understand how to compile proxytunnel either. can someone tell us how to do this? (sorry for such a newb question, but i have googled around quite a bit) thanks

  6. Mark says:

    >>how to compile proxytunnel?

    I first installed the latest XCode Tools, including the unix developer tools, then installed macports from the binary installation from there website. Proxy tunnel can then be compiled and installed using a simple macports command

    Unfortunately running macports also has issue behind a firewall. See the following to fix this.

  7. Mark says:

    I too have the SSL certificate issue. However Pressing Continue doest work. The dialog keeps reappearing. pressing show certificate, and always trust makes no difference either.

    The certificate details are “Unable to display this certificate”, “the data does not appear to be a valid certificate”

    It is as if is wasn’t receiving a certificate. Any Ideas?

  8. Paul says:

    To solve the SSL issue:
    Change the port to 443 like so:
    sudo /usr/local/bin/proxytunnel -a 9090 -p your.proxy:8080 -d

    Then configure iChat to use server localhost and port 9090

  9. Richard says:

    Paul, I was able to get iChat to work with your last post using port 443 but haven’t successfully run a Video Session. Are you aware of any further config that would allow for that functionality?

  10. Naveen says:

    Can anyone tell me what to copy in/usr/local/bin.
    I’ve downloaded proxytunne1.9.0 and unpacked it with stuffit and I’ve got many files in that folder.
    which file do I need to copy ????

  11. sachin says:

    hi friend

  12. Kevin says:

    Is there any way to revert the changes proxytunnel makes to your computer’s networking?

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