Anonymous Email – Step one: You need PGP

August 2nd, 2007 | Posted in Anonymity, Internet, Privacy, Software, Tutorials | 6 Comments

One of the topics that I’ve been planning to cover here involves how to send anonymous email because I want to talk about how to blog anonymously and in order to do that, you need to be able to send email that cannot be traced back to you.

Before I go any further I want to make it clear that while I believe that it’s important for people to be able to use tools like this, I want to say that if all you want to do is say something nasty to somebody without them knowing that it was you then you’re far better off skipping this whole subject.  There is something of a learning curve involved in this and there’s no sense in spending the time and effort to learn something if all you’re going to do is be offensive or harrass people.  You’d be better off venting your frustrations in some other way.

There are plenty of reasons besides anonymity related issues for using PGP encryption and / or signing.  Text and files can be encrypted to be kept safe from prying eyes, text messages and binary files can be digitally signed to assure that they haven’t been tampered with and to assure where they come from.  If a signed message or file has been altered, then the signature will not be valid.

The signature makes you certain of where something came from because only the person who owns the key should know the passphrase for that key which means that nobody else can send a message signed with my key because I’m the only one who knows the passphrase.  Another thing the signature tells you is when something was signed because the date and time is included in the signature.

PGP, or the freeware, open-source GnuPG software is actually pretty easy to install and use.  You can download a freeware version of PGP.  It’s an older version but the advantage is that it’s free and will serve most purposes nicely.

I want to say that GnuPG is an open source freeware package that is up to date and can be obtained from their download page.  GPG Shell is a freeware windows friendly front end for GPG.  GPG is the more current software and for most purposes it is what I use.  However the anonymity tools I’ll be talking about in upcoming entries are designed to work with certain versions of PGP, version 6.5.8 being the best overall choice.

There are those who would say that it’s not a good idea to use older versions of software and try to talk you into getting version 8 or 9.  Don’t let ’em talk you into it.  You’d just be spending a lot of money on something that the software I’m going to cover cannot use.

I have both PGP 6.5.8 and GPG 1.4.7.  They don’t conflict with each other nor do they take up excess amounts of space.

A few years ago I wrote a series of tutorials about how to install and use PGP.  The introduction page also has some links on it for some useful pages to help new users learn how to use it.

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6 Responses to “Anonymous Email – Step one: You need PGP”

  1. Congratulations on being Pay Per Posts blog of the day.

  2. Thanks!  That IS pretty cool isn’t it?

  3. Now that I’m older, I wouldn’t go to the trouble of sending an anonymous e-mail.  However, this information would have been invaluable to me as a bored high school student.

  4. I know what you mean.  However I think that in the age where government and business are getting more and more into everyone’s private matters.

  5. Please notice that when sending a PGP email you are not anonymous since your IP address still shows up in the email header!

    A better title would be SECURE EMAIL instead of ANONYMOUS EMAIL.

    For people who have not installed GnuPG on their PC, an alternative would be where you can send PGP secured email via a web interface.

  6. I never actually said that PGP emails were anonymous.  Rather I’m saying that the process I’m describing of sending anonymous emails require PGP.  Any headers in the email are stripped out long before it is delivered at the final destination.

    Also, with no disrespect intended to your service, I persoally avoid using web based security like that because I would rather have sole control of private keys and such.  PGP and GnuPG give me that ability.  Not only that, they can be had for free.