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How secure is your e-mail? Consider this: With every e-mail you send,
you may be leaving a copy on your computer, with your ISP (Internet
service provider), on the recipient’s computer, and with her ISP.
If either of you are on a network, a copy might rest on the network
servers, as well. Every computer that the message passes through as
it bounces around the world to its destination may have a copy of the
message, and it doesn’t stop there. All it takes is a simple piece of
software to monitor and intercept e-mails (either generally or based
on specific keywords), and government initiatives such as Carnivore
have been intermittently filtering massive amounts of messages much
as a whale filters plankton.
No, your e-mail is not secure, but PGP
(Pretty Good Privacy), an encryption program from Network Associates,
is working overtime to try to correct this. With PGP, you can encrypt
e-mail, files, and other communication methods such as ICQ. Anyone
receiving an encrypted message will only see a collection of random
figures unless they have the means to “decode” the message. You can
also use PGP to create digital signatures, which verify that messages
and files actually came from you and not someone pretending to be
you. By using both encryption and digital signatures, you can ensure
that messages and files exchanged between users are authentic and
unaltered, not to mention private.
The PGPtools menu gives you quick access
to a variety of tasks, including encrypt, sign, and wipe.
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PGP is highly effective, easy to use, and packed with features, and
it has even more than that going for it. It is the de facto standard
for e-mail encryption, providing a solution that users have ported
to a number of different platforms, including Macintosh, DOS, OS/2,
and Unix. Official and third-party plug-ins expand its use, letting
you easily use it with leading e-mail clients such as Outlook, Outlook
Express, and Eudora. It is also free for noncommercial use (as PGP
Freeware), although you can get a more comprehensive version, PGP
Personal Security, that offers additional features such as a built-in
firewall, hard drive encryption, and tech support. A number of different
PGP solutions, free and otherwise, are available from the Network
Associates Web site at http://www.pgp.com/
. We’ll show you how to install and use the PGP Freeware version 7.0.3
for Windows so you can start protecting your privacy.
Installation. After you download
PGP from the Network Associates site, you’ll need to install it on
your computer. Start by closing all applications on your computer
(especially e-mail applications). Unzip the PGP installer and save
it to your hard drive. (PGP is zipped, or compressed, to make it smaller.
If you don’t have a zip program, you can download WinZip at
http://www.winzip.com/
). Double-click the PGP EXE (executable) file to begin the installation
process.
Using PGPkeys, you can search key servers
for public keys and import them to your keyring.
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The installation of PGP is similar to the installation of other applications:
PGP’s Installation Wizard will walk you through the process; you just
have to follow along. When you have installed the software, you will
come to the Key Generation Wizard, which will help you create a key
pair. The key pair is the essence of PGP; it consists of a public
key and a private key. You will give the public key to people to whom
you plan on sending encrypted messages, and you’ll keep the private
key to yourself.
The Key Generation Wizard asks you to assign a name and e-mail address
to this key pair, followed by a passphrase (password) that’s at least
eight characters long. (See the “How Secure is Secure?” sidebar for
more information on creating effective passphrases.) The Key Generation
Wizard will then create your keys and assign them to the appropriate
files on your hard drive. We’ll talk about this more in a minute.
Reboot your system; when it finishes loading, PGP should be set to
go.
Manage Keys. As we mentioned,
the concept of the key is central to PGP. These keys are basically
really large numbers that you generate when you first load PGP. (You
can create new keys any time so you can have multiple keys for a variety
of uses.) The bigger the key, the more secure the ciphertext
(encrypted or encoded data); PGP allows public key
sizes up to 4,096 bits, which roughly translates to very, very
secure.
When you make keys, PGP stores them in one of two files, known as
keyrings, on your hard drive (usually in the PGP folder): Secring.skr
for private rings, and Pubring.pkr for public rings. You should try
to back up these files regularly. You can set up PGP to back them
up automatically upon closing by clicking the PGP icon in the System
Tray, choosing Options from pop-up menu, clicking the Advanced tab, and
checking the Automatic Keyring Backup When PGPkeys Closes checkbox.
Key servers. In addition to putting your own
public keys on the public keyring, you’ll also want to add the public
keys of those users who will be sending you encrypted or signed messages.
You can search for public keys in databases called key servers, and
you can place your own public keys here so others can find them. (This
is a good reason to use your real name and e-mail address when first
creating a key pair on installation; others will be able to identify
your public keys easily.)
To search for the public keys of other users from key servers, click
Start, Programs, PGP, PGPkeys. Choose Search from the Server menu
and select a server to search. Specify search criteria and click the
Search button. You can easily import keys to your local keyring by
right-clicking the key and selecting the Import choice.
In the PGP Options dialog box, you can
set PGP to automatically encrypt and sign outgoing e-mail messages.
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To add your own public key to a key sever, select PGPkeys from the
System Tray icon and highlight a public key to submit in the window.
Then choose Send To from the Server menu and select a key server.
You can also include your public key on your Web site, e-mail it to
people, or just put it in a signature file so that it will be present
in any e-mail you send out.
PGP Components. A
number of different components and tasks make up PGP, and as you might
expect, there are a number of different ways to access them. The first
thing to do is check the application with which you want to use PGP.
Many applications, such as e-mail programs, have built-in support or
plug-ins for PGP that put menus or icons right in the program itself.
This makes it easy to access PGP tasks such as encrypt, sign, decrypt,
or verify.
Alternately, you can access many of the PGP utilities (such as PGPkeys,
PGPtools, PGPtray, PGPnet, and documentation) by clicking Start, Programs,
PGP and then making your choice from the submenu. Additionally, a
PGP icon in the System Tray gives you easy access to many of these
utilities and more (such as PGP Options). If a PGP icon doesn’t appear
in the System Tray, click Start, Programs, PGP, PGPtray.
Now that you know where to find them, here are some of the primary
components that make up PGP.
PGPtools. PGPtools gives you access to a number
of different tasks you can accomplish in PGP, including encrypt, sign,
decrypt/verify, and wipe. It also gives you quick access to PGPkeys.
Opening PGPtools puts a floating menu on your Desktop. To use one
of the tasks on the bar, just drag a file over it or click the icon
and select a file to work with. It’s handy to have PGPtools open if
you’re working with an e-mail program that does not provide support for
PGP.
The last two icons on this floating menu are Wipe and Freespace Wipe.
Wipe lets you overwrite files, and Freespace Wipe lets you overwrite
sections of your hard drive so that any lingering data is completely
destroyed. This is important because most of the time when you delete
something from your computer, it is set aside to be overwritten as
necessary. This can leave sensitive data open to recovery, but these two
utilities can completely remove them from your computer. You can also
set Wipe up so that it automatically wipes files when you delete
them.
Current Window. This feature lets you perform
cryptographic tasks such as encrypt or decrypt automatically in the
window you’re currently working in. When you choose an option from the
Current Window submenu, PGP copies text in the active window to the
clipboard and performs the task you selected.
PGPnet. This module makes it possible to securely
communicate with other PGPnet users. Users can create a Virtual Private
Network to share data or just communicate through a secure
tunnel.
PGPkeys. You can use this feature to create,
view, and work with your own keys and the public keys of others. With
PGPkeys, you can search for public keys, work with groups (to share
encrypted mail with more than one user at a time), and more.
PGPdisk. Available only in the retail version
of PGP, PGPdisk lets you set up a file that can be “mounted” on your
hard drive, letting you create a secure “drive” on your computer.
Use PGP For E-mail.
One of PGP’s primary functions is to let you send and receive secure
and digitally signed e-mail. PGP makes this task easy by coming bundled
with a number of plug-ins that let it work automatically from within
programs such as Outlook and Eudora. To send e-mail using PGP to another
user who has a PGP-capable e-mail program such as Outlook, click the
PGP icon in the System Tray and choose Options. Click the E-mail tab
and click the Use PGP/MIME When Sending E-mail checkbox. If your recipient
does not have an e-mail program that supports PGP, leave this box
unchecked.
In e-mail programs such as Outlook, you
can access PGP either through the PGP menu or the icons on the
button bar.
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Now you’re ready to send safe, encrypted messages. When you’re finished
typing an e-mail message you want to encrypt, click the envelope and
padlock icon to encrypt the message (click the paper and pencil icon
to sign the message) or choose the correct option from the PGPtools
menu. You can also choose to have PGP automatically encrypt and sign
new messages by checking the appropriate checkboxes in the E-mail
tab of the PGP Options dialog box.
PGP will automatically select the appropriate public keys from the
keyring when you send the message. If PGP doesn’t recognize the recipient,
the PGP Recipient Selection dialog box will appear. You can automatically
open this dialog box by pressing the SHIFT key while clicking the
Send button. Drag the correct public key into the recipient list box
(or search a key server for the recipient) and click OK to send, then
enter your passphrase when prompted.
When you receive an encrypted message, you can decrypt and verify
it in several ways. One way is to select the Decrypt/Verify icon from
the PGPtools toolbar. Another way is to click the appropriate icon
from your e-mail program button bar. You can also make your selection
from the PGP icon in the System Tray. You can save messages either
in their encrypted or decrypted state. Of course, it’s safer to save
them as encrypted files.
Use PGP For Files. In addition
to e-mail, you can use PGP to secure files on you hard drive either
for storage or to send as enclosures or distribute on disks. As with
e-mail programs not supported by PGP, you can use PGP tasks such as
encrypt and sign by choosing them from the PGPtools toolbar (or by
dragging the files to one of the PGPtools menu icons) or the PGP System
Tray icon.
Legal Issues. PGP
is a great way to encrypt and digitally sign documents and files,
and you can’t beat the price. Depending on the country you live in,
though, it may be illegal or subject to restrictions. To find out about
the legal status of cryptography in countries around the world, check
out the Crypto Law Survey at
http://cwis.kub.nl/~frw/people/koops/lawsurvy.htm
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by Rich Gray
How Secure Is Secure?
PGP is pretty darn secure, at least in terms of brute force
attacks. According to the FAQ kept by comp.security.pgp, it would
take a billion computer chips capable of a billion key attempts a
minute 10,000,000,000,000 years to check out all the possibilities
for a 128-bit key. That doesn’t mean, however, that PGP isn’t
infallible. Many of the vulnerabilities that can befall PGP
come through less direct routes. Here are a few to watch for.
Sloppy passphrase management. One of the biggest causes of security
problems in PGP is human error in terms of choosing and handling
passphrases. Many users write down their passphrase and then
accidentally let it fall into the wrong hands, or they choose a
passphrase that is too easy for someone to guess. This is a problem
because once someone has your passphrase, she can access your
messages and create signatures.
To select a secure passphrase, make sure it is not a single
word, a common phrase, or a phrase or word closely associated
with you or your family. Add numbers to it to make it more difficult
for others to guess. Also, make sure that the passphrase you
choose is easy enough for you to remember so you don’t have
to write it down. You should also make sure that others haven’t
tampered with public keys and that they aren’t phony. You can
thwart so-called man-in-the-middle attacks, in which forged
keys are made publicly available, by using digital certificates
to verify that they are genuine.
Beware Trojan horses. Malicious viruses can strip your system
of keys, passphrases, and deciphered messages. Keep your virus
detection software up to date, and make sure that you only download
copies of PGP from trusted sources, such as Network Associates.
Because it is an open source program, anyone can tamper with
PGP and try to pass a corrupted copy off as the real deal.
Keep your computer and information safe. If your computer is
part of a network, you are especially at risk for hacking attempts.
Try to keep PGP and sensitive information on a single-user system
if possible. Save files in encrypted format on your computer
and use PGP’s Wipe utilities to truly delete files and make
sure that sensitive data is completely erased. Also, consider
looking into software that will periodically overwrite your
swap file. (Your computer’s virtual memory uses the swap file,
and it may contain sensitive information.)
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