Understanding how information stays secure can help you make informed choices about your encryption strategies.
Keeping Your Secrets Secret
Understanding how information stays secure can help you make informed choices about your encryption strategies.
Encryption. The word alone makes us think of something
we’d rather not know. It sounds too hard. Too mysterious.
Like something the cat dragged in. Enter the Internet.
Bring on e-commerce. Suddenly we recognize our vulnerability
and our need for veracity.
Because we want to keep our information secure, we have
to implement some kind of encryption or use a PKI or contact
a vendor for certificates or… But wait. Before you rush
off and implement an unsound or unnecessarily expensive
strategy, let’s discuss cryptography, the science of creating
cryptographic algorithms. Cryptoanalysis is the science
of breaking or cracking messages that have been encrypted
using those algorithms. Encryption is the process of changing
the appearance of a message by applying a cryptographic
Aww, Yeech. It’s Mathematics
As you begin your research, you’ll be exposed to one
overwhelming fact—it’s the mathematics, stupid. Don’t
worry! Even though most of us don’t do much with that
graduate-level math stuff, my purpose this month is to
expose you to encryption and the many ways it can be applied—not
to encumber you with the intricacies of the mathematics
that lie behind it. I’ll give simple examples. I’m hoping
that this knowledge will help you understand the processes
being used to secure your data and help you make informed
choices about your encryption strategy. Remember, the
examples are simple, the algorithms are simplified; to
learn more, visit the resources listed at the end.
Long, Long Ago, and Far, Far Away…
Caesar has been credited with the use of the first algorithms
for obscuring data. The earliest attempts were to disguise—you
guessed it—troop movements. A strip of papyrus was wrapped
around a stick of wood, spiraling from one end to the
other. The message was written down the length of the
stick on the paper. The papyrus was unwound and, behold,
the message was unreadable. A runner was dispatched with
the message. A general at the receiving side had a stick
of wood with exactly the same dimensions. Winding the
papyrus back around the stick made the message clear.
If the runner was captured, the enemy would have a hard
time understanding the message. The name of the stick?
A cipher. This is an example of encryption where the algorithm
Later, Roman troop movements and other secrets of state
were disguised by using simple replacement algorithms.
Each letter in a message was replaced by the next character
in the alphabet, or some other simple character-for-character
substitution. The monoalphabetic substitution cipher was
Fast forward. In the 1700s letters were replaced with
numbers and values were added to the numbers to make the
task of deciphering the message much harder. For example,
replace each letter of the alphabet with a number. A becomes
01, b becomes 02, etc. Use this key to replace each letter
in a message. Then add 3 to each number in the message.
So the letter A becomes 04, B becomes 05, Z becomes 29,
and so on. A simple message such as, “I am going to kill
the king.” becomes:
12 0416 1018121710 2318 14121515 231108
Decryption reverses the process. Subtract three from
each number and look them up on your alpha-to-numeric-to-alpha
This simple encryption algorithm uses the same number
(three) or key in the process (look up the letter on the
chart , add three, or reverse), so it’s said to be a symmetrical
key cryptographic algorithm.
Next, letters were substituted by using two alphabets.
One alphabet was used for the odd characters in the message,
another alphabet to replace the even characters. These
combinations are known as polyalphabetic ciphers. To see
how this might work, number the letters of the alphabet
from 1 to 26. Next, for the odd position alphabet change
each number by adding 3 to the number before. (1 stays
as 1, 2 becomes 4, 3 becomes 7, 4 becomes 10, and so on.)
For each letter take the results and find the modulus
26 (or mod 26) of this number. The modulus is the remainder
left after simple division. Let’s do a few. 1 mod 26 is
1, 4 mod 26 is 4, 28 mod 26 is 2. Replace each letter
of the alphabet with the letter represented by this result.
So A remains A, B becomes D, J becomes B. The alphabet
for odd positions becomes:
To create the even alphabet, use the number 5 instead
of the number 3 and add 13 to the result before taking
the modulus 26. A or (1+13) mod 26 becomes 14 or N. B
or (6+13) mod 26 becomes 19 or S. The alphabet for even
Many variations of these algorithms have been used in
Like the papyrus cipher, the alphabetical algorithms
relied on the fact that the algorithm was unknown.
Its Power Is in Its Exposure
Like the ancient ciphers, modern encryption uses numbers
as keys. The numbers are just larger—very much larger—and
the algorithms are known. Well-known algorithms can be
examined by everyone, and everyone has a chance to find
problems with it. Over time the successful algorithms
(those that keep private data private) are easily identifiable—they’re
still used and discussed. You don’t have to know higher
mathematics to determine if the algorithm you’re choosing
is a good one; you can rely on people who know the math
as well as how to test the algorithm to help you identify
the one you need. But the algorithms are known? How can
that be? Doesn’t that mean others could decrypt the messages?
The well-known algorithms used today rely on something
else, some quantity that must be used with the algorithm
for it to work. That something else is either something
both parties know—a shared secret—or something each has
a part of—key pairs.
Shared Secrets and Key Pairs
If we wish to send confidential documents between my
city and yours, we could invest in a lock box with two
identical keys. Each of us has a key. I place my documents
in the box, lock it with my key, and send the box your
way. On its journey, no one else can unlock the box and
get at its secrets. (Well , they could hack in, but that’s
another discussion.) When it arrives, you unlock it with
your key and retrieve the documents. The algorithm, a
locked box that requires a key, is well known. The item
that keeps our documents private is the shared secret—the
key. We each have the identical key. This is, of course,
just a modern version of Caesar’s cipher—a symmetrical
key cryptographic algorithm. The difference: The algorithm
But what if I don’t want us to have the same key? We
have a lock box with two keys. One locks it and one opens
it. I lock the box with my key; only your key can open
it. You lock it with your key; only my key can open it.
We each have a key, but they’re different. One key is
the inverse of the other. This is known as an asymmetrical
key cryptographic algorithm. It’s the basis for public
key cryptography. Since binary numbers don’t come with
padlocks, how is this done? Here’s where the mathematics
Our modern-day key pairs are factors. As you recall,
if I multiply two numbers, I get a product. If I know
the product and one of the numbers, I can get the other
number. If that other number were used in an encryption
scheme, I could then decrypt the message. Since we all
know the multiplication table, what makes the key secure?
If the product has as its factors sufficiently large prime
numbers, the knowledge of the product’s factors is sufficiently
obtuse to keep it secret. But if I know one of them, I
can discover the other.
Modern Algorithms and Implementations:
Unlike early algorithms, the Data Encryption Standard
(DES) algorithm (a symmetrical key algorithm) is published
and available to anyone. The security of messages using
this standard is similar to the security of the locks
on your car or house—they rely on the protection of the
The DES key is 56 bits long. No one, it seems, could
ever guess which key you’re using.
Wrong. In June 1997 some folks used a brute force approach,
in which every possible key was tried, one after another;
the attack put a large number of computers working in
parallel for 140 days to find the correct key. DES is
now considered to be fairly easy to break with modern
Of 963 security products examined in a recent survey
by Trusted Information Systems, 466 use DES.
A variant of DES, Triple-DES, uses DES three times with
three different unrelated keys, thereby strengthening
R2D2, er… RC2 and RC4
Modern cryptography recognizes that computers can break
symmetrical key algorithms. RC2 and RC4 use key pairs
and are asymmetrical key cryptographic algorithms. Each
key pair consists of a public key and a private key.
These proprietary and until recently unknown algorithms
are owned by RSA Data Security, Inc. Keys of selectable
varying length may be used.
RC4 is the algorithm used in Netscape’s Secure Sockets
Layer (SSL) communication protocol (the one used to encrypt
your credit card when you purchase items over the Web).
Up to 128 bits can be used in the key.
A message encrypted with a 40-bit key was decrypted after
using a brute-force attack to recover the key. This took
only 3.5 hours.
The algorithm uses very large prime numbers to generate
a public and a private key. When very large prime numbers
are used, it’s almost impossible to factor out the private
key if you know the public key. Since the RSA algorithm
is very slow, it’s often used to encrypt a symmetrical
key; then the encrypted key is used to encrypt the rest
of the data. The symmetrical key is randomly generated;
therefore, only the private key can be used to determine
Other symmetrical and asymmetrical key algorithms in
use include IDEA, SkipJack, El Gamal, Blowfish and Diffie-Hellman.
A newer type of algorithm, Elliptic curve public key cryptosystems,
is in testing. See www.ssh.fi/tech/crypto/algorithms.html.
Public Key Cryptography
Say you want to securely communicate with members of
your company and trading partners over the Internet. How
do you set up a secure transfer of keys? How can you implement
a strategy that doesn’t overwhelm you with its details?
Public key cryptography allows the secure exchange of
messages in a public environment. It relies on the use
of two keys that are the inverse of each other.
Your public key is published—available to everyone. Your
private key is held by you alone. I’ll use your public
key to encrypt (using RSA or El Gamal) my message before
sending it to you. Only you know your private key, so
only you can decrypt the message. Want to be sure I really
sent the message and that nobody changed it? I use my
private key to seal the message—you can use my public
key to unseal it. (See, “Integrity Protection” on the
following page.) So how do you publish your private key?
How do I find it? Where do I get a public and private
key pair? Some companies have chosen to implement their
own Public Key Infrastructure (PKI); but you can obtain
a key pair and make your public key available by contacting
Verisign at www.verisign.com.
(I’ll cover PKI in a future column.)
Kerberos (in classical mythology, Kerberos the three-headed
dog guards the gates of Hades) was originally developed
to guard the resources of MIT from its creative students.
A Kerberos server or Key Distribution Center (KDC) is
used to authenticate users. Only the server and the user
know the password. The Kerberos server can set up a secure
communications channel between two authenticated users
by issuing Kerberos tickets, one for each user. Each ticket
identifies both parties, is time-stamped (to prevent its
use or misuse—such as a replay attack), and contains a
time duration (how long the ticket is valid) and a session
key. Tickets are encrypted using the users’ passwords;
thus only the users can read the tickets and obtain the
session key. The session key is then used to encrypt a
message. The first message includes the ticket key for
the recipient. When both users have the session key, secure
communications can proceed. [For a technical explanation
of Kerberos, read Michael Chacon’s column, “A Matter of
Security,” in the May/June 1997 issue.—Ed.]
Choices, Certificates, and the Spy
So,where’s the beef? You know you don’t want to clutter
up your system with all these keys or key pairs. Isn’t
the question for most of us not which algorithm to use
but which product to choose? And can’t all of these fancy,
schmantzy algorithms be broken?
You’re right on all accounts. But, you still have to
put the lock on the box. The question of whose lock and
where to store the keys isn’t easy to answer, nor can
it be resolved in this column. On the other hand, the
implementation of your chosen strategy may be easier than
you think. The processing and key storage and sharing
happens under the hood, and you may have as little to
do with it as you choose. Keys can be stored in certificates,
which can be handled by third-party trusted organizations.
You can implement a Public Key Infrastructure or your
own as well and become part of a certificate hierarchy
in which certificate authorities trust other certificate
authorities. To share data within your organization or
simply to protect data on digital devices, use a product
that implements the algorithms I’ve discussed here.
The reality is, you and your peers will be using these
technologies very soon now, especially PKI, and the time
to learn more is now.
As the spy whispered to me when last we tangoed, “In
the future I see three types of computer professionals:
Those who develop and implement PKI, those who use PKI
to their advantage, and those whose biggest challenge
will be to ask, ‘Would you like some fries with that burger?’”