Encrypting IM With Pidgin On Windows

By Randy Jensen | Aug 21, 2007

windowslivewriterencryptingimwithpidgin ec0bpidgin thumb12 Encrypting IM With Pidgin On Windows So I’m slowly moving away from all proprietary software that I currently use. Next on the list, Windows Live Messenger.

The major thing holding me back was I needed a client that supported RSA encryption since I tend to do a bit of IM’ing at work and I don’t want people viewing my messages over the tubes. MSN Messenger and SimpLite worked perfectly together and if it’s not broke…

Well, I’m making the switch to Linux soon and I don’t want to be bound by any software. The only issues I currently see are Photoshop and Dreamweaver. Other than that, game on.

  1. Download Pidgin (formerly GAIM)
  2. Download Pidgin-encryption (direct link – Win32 self-extracting binary)
  3. Install Pidgin and then install Pidgin-encryption (in that order)
  4. Open Pidgin and add all of your IM accounts
  5. Go to ‘Tools’ –> ‘Plugins’
  6. Look for Pidgin-Encryption and check the box next to it and hit close
  7. That’s it:)

Now, you have a couple of paths to take. All of my friends aren’t quite at the level where they really care about encrypting their IM’s, so I don’t want to encrypt all messages.

What I do is go through my contact list and find the people I know are also using encryption and right click their name and choose ‘Turn Auto-Encrypt On’.

windowslivewriterencryptingimwithpidgin ec0bautoencrypt3 Encrypting IM With Pidgin On Windows

If everything is working correctly, you should see two green locks on the upper right hand of your message window. If you only see one, that means that you are asking for encrypted messages, but the other person does not have it enabled.

windowslivewriterencryptingimwithpidgin ec0bgreenlock3 Encrypting IM With Pidgin On Windows

The other option is to go into the plugin configuration settings and tweak them to your liking (the defaults worked fine for me). To get there: ‘Tools’ –> ‘Plugins’ –> highlight ‘Pidgin-encryption’ and click the ‘Configure Plugin’ button.

windowslivewriterencryptingimwithpidgin ec0bsettings3 Encrypting IM With Pidgin On Windows


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  • Richard
    Can pidgin-encryption enable me to talk to friends who use MSN Messenger plus SimpLite? It seems like it should be if we could figure out how to exchange keys.

    Can you give any advice on how to exchange keys with an MSN/SimpLite user please?
  • Francesco
    I personally prefer to use off-the-record messaging. It is available for Pidgin and Miranda-IM, and comes built into Adium.
  • So you're talking about the hand-off that happens when you are logging into your account and the MSN servers. That's a very interesting question.

    I actually didn't know Hotmail had added the secure login to all logins, so thank you:) Gmail was the first I knew of to offer secure login (however, once you are logged into your email, it goes back to http and you must explicitly type in https to stay in secure mode. it would be too much of a strain on their servers to stay in secure mode for everyone).

    I honestly have no idea if the logins are passed through a secure connection or not. I would imagine that since the logins are tied to the webmail accounts, that all major IM clients would take measure to at least encrypt the login info...but look who we are talking about here:)

    I did some quick research and wasn't able to come up with anything, but good luck. I hope you find your answer! Sorry I wasn't much help:(
  • Frank Wikstrom
    Hi, thanks for the speedy answer. I have noticed that when logging in to hotmail the credentials are sent over https, so I assume ir is the same with msn messenger. The chat messages then get sent unencrypted, just as the hotmail inbox is sent in cleartext for instance. But for me the security of the login credentials is far more important than the messages. To my surprise I havent found anything about that on the net. I have checked the faqs for pidgin and other msn messenger alternatives.
  • Hey Frank, I'm really not sure about the MSN network. When I was using MSN, I used SIMPLite to encrypt all my messages.

    I'm not completely sure what you are referring to when you say "out of the box" because with MSN, there is no encryption built in. Everything is sent as plain text over the network.

    As far as SIMPLite, the two chatting had to exchange and verify RSA keys in order to begin the conversation. This meant that the line was secure before the message was actually sent.
  • Frank Wikstrom
    Encryption sounds good, but is the authentication secure, always, out of the box, in the case of the msn network ?
  • Hey Adam, of course! Let me know if you have any issues that I can help you out with.
  • Thanks for the guide :) going to try it out later.
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