Get comfortable with using PGP encryption by itself. Find a friend who
uses it and exchange keys. Then, get yourself a remailer client.

As for which one to choose: well... the short answer: Quicksilver or
Jack B. Nymble.

The long answer: I have listed a handful of remailer tools below.
There are a handful of others (Anonpost, Crusader, John Doe...) I've
chosen to highlight the ten programs below because they are the ones
that are readily available on the Internet and free of charge.
However, I would add a word of warning before trying these programs:

To my knowledge there currently does not exist a remailer client that
functions "out of the box". All remailer clients (especially the ones
that are no longer maintained) require a certain amount of tinkering
and configuring to make them work with the current crop of remailers
and stats URLs. Just so you know...

I highly recommend QuickSilver because it is one of the only programs
out there that is actively being maintained and developed. If you've
spent any amount of time in APAS you'll have seen many Quicksilver
updates announced there. JBN is great too. And you'll find answers to
your JBN questions simply by lurking here in APAS.

For Windows:

QuickSilver <http://quicksilver.skuz.net/>
Finally, Mixmaster made easy! This free program is the newest of the
remailer clients. It's a Mixmaster email client program. It can send
anonymous email and post anon articles to newsgroups via Mixmaster
remailer chains. QS, itself, doesn't possess any encryption
capabilities. Instead, it serves as a GUI "front end" to Ulf
Möller's Mixmaster 2.9beta.

Recently, QS author Richard Christman has written a PGP-plugin for
Quicksilver. <ftp://skuz.net/pub/quicksilver/> So now it's not only a
Mixmaster client. It's a Cypherpunk remailer client as well!

Jack B. Nymble 2 <http://www.bigfoot.com/~potatoware/jbn2/index.html>
(From the User's Manual:) "Jack B. Nymble 2 (or JBN) is a feature-rich
Windows email client which facilitates the use of anonymous remailers
for anonymous email and newsgroup posting. It includes ease of access
and automation for beginning users, as well as sophisticated control
of remailer messages for more advanced users. Support is included for
PGP encrypted messages, Mixmaster messages, attachments, and MIME
mail. JBN2 also includes support for nym mail and nym account
reply-block creation (see #7.1-#7.4), centralized queuing and sending
via SMTP, POP3 retrieval, NNTP retrieval, and automated nym mail
decryption. It also includes a mini web browser used for downloading
remailer reliability statistics, keys, and web pages. Support is
included for PGP versions 5.5.3x and 6.x, in addition to DOS version
2.6.x. Mixmaster 2.0.4 is also fully supported."

Also, excellent documentation and help files can be found at the
Potatoware Homepage <http://www.bigfoot.com/~potatoware> .

Private Idaho <http://www.eskimo.com/~joelm/pi.html>
P.I. is an email client for Windows which simplifies the creation and
the sending of anonymous remailer messages. It also simplifies the
creation of nym accounts and the sending/receiving and decryption of
nym messages. It is available in both 16-bit and 32-bit versions. A
properly installed version of PGP is required. Additionally, Mixmaster
messages can also be created and sent if Mixmaster is installed on
your computer.  The author, Joel McNamara, no longer maintains this
program and it's age is showing.Trying to make PI do what you want it
to do is probably more trouble than it's worth. If you want to give it
a go I would recommend the 16-bit version by Ian Lynagh
<http://www.lynagh.demon.co.uk/pidaho/> with source code available.

See also this excellent page of FAQs related to Private Idaho
<http://www.dnai.com/~wussery/pgp.html> and Thanatop's tutorial on
Remailers, Nyms and Private Idaho <http://www.skuz.net/Thanatop/> .

Potato and Decrypt <http://www.bigfoot.com/~potatoware/pot/index.html>
Potato is a freeware DOS remailer client which operates well in
Windows. This software prepares anonymous messages which are then
mailed using your email client. Decrypt is a mail decryption utility
provided with Potato, available as a separate application. These
programs are early creations of RProcess the author of both JBN and
the Reliable Remailer <http://www.bigfoot.com/~potatoware/reli/> - a
popular remailer server for Win95/98.

Mixmaster <http://www.thur.de/home/ulf/mix/> 
For DOS users there is Mixmaster v 2.0.4. For DOS/Windows users
Mixmaster 2.9beta is what you want.These are the two versions that are
most commonly used. Mixmaster can be used by itself as a client or as
remailer. But for Windows users we suggest using one of the excellent
GUI clients mentioned above in concert with Mixmaster.

For Mac:

Mixfit (aka Macmixmaster)
<http://www.geocities.com:80/SiliconValley/Byte/6176/macmixmaster.html>
A Mac Mixmaster Client. Like Potato this program does not mail the
Mixmaster message that it has created. You must cut and paste it into
your favorite email client.

For more Mac encryption and security-related downloads try here
<ftp://erg.ucd.ie/Public/Macintosh/Cryptography/> and here
<http://www.shopmiami.com/prs/fritz/macpgp.htm> ; For a variety of
interesting email-related software including a Mac Remailer(!) called
AnonAIMouS try here
<http://download.uni-hd.de/ftp/pub/mac/info-mac/comm/inet/mail/> ;

For Unix/Linux:

Mixmaster <http://www.thur.de/home/ulf/mix/>
Mixmaster for the Unix/Linux OS. The same executable can be used as a
client or as a remailer. The remailer can be installed on any *nix
account that can receive mail. Non-remailer messages will be delivered
as usual. If you have root access, you may want to create a new user
(e.g.,`remailer') and install Mixmaster under that user id. The
iInstall script provides a simple way to set up the remailer.

As a remailer Mixmaster can be configured to additionally accept and
process Cypherpunk remailer messages. In fact, this is the way most
remailers run today: as a hybrid of Cpunk and Mix.

Premail <ftp://dl.xs4all.nl/pub/mirror/munitions/network/email/>
Premail is an older but still useful program written by Raph Levien
for use with remailers. It fully supports the creation of Cypherpunk
and Mixmaster messages. Perhaps most useful is its ability to create
and manage nym accounts with good security and easy commands.  In
addition to being a remailer client, Premail supports PGP and S/MIME
for standard secured Internet e-mail. It works with mh, elm, Mutt and
newer versions of Netscape. It requires Perl to be installed on your
computer.

The RemOp of the now defunct Septic Remailer warns: "Premail breaks
when fed mail to a nym which has been signed with something other than
PGP 2.6.x."

See also <http://www.debian.org/Packages/unstable/mail/premail.html>.

SendNym
<http://www.driveway.com/web/share.jsp?sid=57794b91.bacca&name=%3DIntern
et&dwSession=vapp03-7be21aa956ea322b&view==0> 
A brand new program by oldhack@nym.xg.nu It takes the place of
Sendmail in relation to your mail client and facilitates the use of
nyms by sending simple nym commands to your mail client, allowing
users to easily switch between sending through their nym or sending
through their regular e-mail account. It will not create a nym for
you. This must be done manually by the user before using Sendnym. It
supports Usenet posting,and random chain selection (through
Mixmaster.)

Sendnym has been successfully tested on Linux 2.2.17 . It requires: a
*nix system with Sendmail, Perl and Mixmaster installed. Also, your
mail client must allow you to configure the name and location of
Sendmail (e.g. Pine).

Mailcrypt <http://www.nb.net/~lbudney/linux/software/mailcrypt.html>
Although not a remailer client, Mailcrypt is an Emacs interface to PGP
and GnuPG <http://www.gnupg.org> encryption with features for
encrypting and decrypting email and news.

See also this page <http://www.worldnet-news.com/software.htm> for
more anonymous remailer clients including the no-longer-maintained
Anonpost, Easynym etc...

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