How to Chat Anonymously Online

A guide to anonymous encrypted communication in 5 easy steps.


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Chatting anonymously on the Internet isn't used solely for shadowy criminal hackers and government operatives. From journalists to congressmen, learning how to adjust the privacy of our digital communication is becoming an ever more important skill.

When Edward Snowden first reached out to reporter Glenn Greenwald, he insisted on only using encrypted communications.

Greenwald's lack of technical skills nearly cost him the story of the century, but with a colleague's help, Greenwald learned how to use encrypted chat servers, a prerequisite to gaining Snowden's trust and a far more efficient and secure method than even encrypted chats or text messages, which can still leave evidence on local devices.

Browsing and communicating on the internet anonymously is difficult, time-consuming, and painstaking. One weak link or careless trace of metadata can expose your identity to the world. But that doesn't mean you need a Master's Degree in computer science to avoid the prying eyes of the NSA. 

In five easy steps, Reason TV shows you the basics of "How to Chat Anonymously Online."

Step 1. Download Tor Browser.

Unlike other web browsers, that store your personal information and browsing history for corporate advertisers and government subpoenas, Tor is completely decentralized.

The user-driven free software reroutes your information through a network of thousands of computers worldwide to hide the user's identity.

Now known publicly through Snowden's revelations, the Five Eyes (the Anglophone allies who frequently collaborate as the greatest global spying behemoth ever known) have admitted being unable to directly de-anonymize any specific Tor user.

And although they have been able to de-anonymize a few random Tor users, they can't do it on demand. 

From this point on, for the purposes of maintaining anonymity, you should always be using the Tor browser when downloading subsequent applications and creating personal accounts associated with those applications.  

Step 2. Use Off-the-Record Chat Servers

Like Tor is for web browsers, Jabber chat servers are decentralized; and unlike mainstream chat services, Jabber doesn't require you to enter any verifiable personal information to create an account. 

The encryption protocol known as Off-the Record (or OTR) allows both sides of a the chat to be encrypted. 

There are literally hundreds of Jabber servers around the world available to use, click on the link to find a recently updated list

Once you've selected a Jabber server, create an account, but remember, only use a server that lets you sign up using the Tor Browser. When creating a username and password, use random number and letter combinations for each account and never use the same name or password twice. Also, be sure to write down this information and keep it in a safe place, uploading this information to an insecure cloud-based server like Dropbox or Evernote or god-forbid, email, puts your security at needless risk and jeopardizes your anonymity. 

Step 3. For Mac Users, Download Adium 

For Mac users, download Adium, using Tor. And make sure to keep your Tor Browser open when using Adium to maintain connectivity. 

There are programs specifically for Windows, but for this lesson, we'll stick with Mac OS X.

Once it's up, ignore the Adium Assistant Window, you can just close it.

Select Adium's drop down box, then choose Preferences. Select the Accounts tab, then click the plus sign to add a new account. Select XMPP Jabber.

I know it's getting a little detailed now, but stick with me. Following these instructions to the letter WILL work. The next steps ensure that Adium will only work using Tor.

Switch to the Proxy tab. Click "connect using proxy," then choose "SOCKS5." 

Type "" into the server field. Create a new username and password. You see where it says, PORT? Type 9150 there.

Go to the Privacy tab, and where it says "encryption" switch it to "Force encryption and refuse plaintext."

Go to Options, and in the Resource box, delete your computer's name and type "anonymous, then check "Require SSL/TLS"

Go back to Account, and type in your Jabber ID (which you created in Step 2), Your ID is comprised of the Jabber username you created in Step 2, followed by an "@" sign, and finally the Jabber server your choice. 

Enter your password, click OK.

Finally, to test your account's connection, switch your status to "available." 

Step 4. Create encryption keys and fingerprints. 

You'll need a key to unlock encrypted messages. 

To create a key, click Adium, then choose Preferences. 

After that, go to Advanced and click Encryption. 

Select your account and click Generate, which will create your encryption key and fingerprint. 

To have an encrypted chat, a person needs to know your Jabber username, server, and your fingerprint. You'll need to know theirs, too. Exchange fingerprints over another communication channel.

Once you've established a new chat, you can verify each other's fingerprints. If they match, mark this person's contact info as "trusted." If they don't match, your communication has been compromised. Either try again at another time, or create new accounts. In fact, Micah Lee, an encryption expert and journalist with The Intercept recommends dumping chat accounts frequently, and even making single use chat accounts when contacting someone for the first time, ensuring you both leave no trace of your true identity. 

Step 5. Verify contacts.

To verify contacts, add a person's Jabber ID (reminder, this is your username plus an @ plus the Jabber server) to your Contacts. 

If the contact is online, you will only be able to see them if they have authorized your contact request. Once they have, you can authorize them back. 

Finally, you can click on the contact and begin chatting. 

Though you've sent a message, you will only be certain your chat is secure if the fingerprints match. Compare them in the OTR Fingerprint Verification box which should pop up after the first message has been sent. 

If every single character matches, you can trust this contact. 

And that's it. Happy anonymous chatting!

About 5 minutes. 

Produced by Anthony L. Fisher and Joshua Swain.

Music: "Mensa," "Dark Water," "Undersea Garden," "Loll," and "Motivate," all by Poddington Bear.  

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