If you’re like most people, you probably have conversations with friends and family on a regular basis. But what about when you want to keep those conversations private? There are a few things you can do to make sure your IM conversations stay private. First, make sure that both parties are aware of the conversation’s potential privacy implications. If one party is not aware of the potential privacy implications, they may be more likely to agree to a conversation without knowing the full consequences. Second, use clear and concise language when discussing sensitive topics. Avoid using words such as “private,” “confidential,” or “sensitive.” These words could potentially reveal too much about the conversation for either party. Third, be prepared for possible objections from your friends and family. They may feel that talking with someone outside of their comfort zone is a good thing, but remember that not everyone is comfortable with off-the-record conversations. Be prepared for them to say things like “I don’t think that’s a good idea,” or “I’m not comfortable with this.” Be honest about why you want to keep the conversation private and be willing to listen to their objections if they arise.


Off-the-Record is a great plugin to keep your conversations private. For it to work both parties need to have the plugin installed. It works by encrypting your conversations so no one can read the IMs. The messages you sent don’t include digital signatures that can be checked by third parties. It also includes an authentication feature so you can be assured the person you’re talking to is the right one.  It’s completely free under the GNU License and works with Windows, Linux, and OS X.

Off-the-Record is available for several IM clients, but we’ll show you how to use it in How-To-Geek’s favorite…Pidgin. 

Installation & Setup

Download and install Off-the-Record (OTR) following the wizard as normal, you don’t even need to close out of Pidgin.

After it’s installed, on your Buddy List go to Tools \ Plugins.

Now scroll down the plugin list and select Off-the-Record Messaging and click Configure Plugin.

Now you’ll need to generate a key and select other options. For instance you might not want to log OTR conversations for added privacy.

Private key was generated successfully…

You can choose different ways to authenticate a buddy such as Question and Answer or a Shared Secret.

After you’ve determined the authentication method you want to use, both you and your buddy need to answer the question or secret successfully and you’re conversation will change to private.

If the authentication doesn’t match, you’ll receive a message indicating so.

It will put an OTR icon on your toolbar where you can control the different settings like buddy authentication.

There will also be a private icon in the lower right corner where you can control different settings as well.

Conclusion

A couple of caveats we saw were it would pop up unverified messages when communicating with people who you don’t need it for. Also, uninstalling it was bit quirky but that doesn’t make it a deal breaker. Whether you’re at work and don’t want the boss spying on your private conversations, or are making plans for global domination, OTR is a great plugin to keep your IMs secure.

Download OTR for Windows, Linux, and OS X