Cryptograph

y and
Network
Security
Sixth Edition
by William Stallings
 Chapter 2
Classical Encryption
Techniques
 "I am fairly familiar with all the forms of
secret writings, and am myself the author
of a trifling monograph upon the subject,
in which I analyze one hundred and sixty
separate ciphers," said Holmes.

—The Adventure of the Dancing Men,

Sir Arthur Conan Doyle
 Symmetric
Encryption
• Also referred to as conventional
encryption or single-key encryption

• Was the only type of encryption in use

prior to the development of public-key
encryption in the 1970s
• Remains by far the most widely used of
the two types of encryption
 Basic Terminology
• Plaintext
• The original message • Cryptographic system
or cipher
• Ciphertext • Schemes used for
• The coded message encryption

• Enciphering or encryption • Cryptanalysis

• Process of converting • Techniques used for
from plaintext to
deciphering a message
ciphertext
without any knowledge
• Deciphering or decryption of the enciphering
• Restoring the plaintext
details
from the ciphertext
• Cryptology
• Cryptography • Areas of cryptography
• Study of encryption and cryptanalysis
 Simplified Model of
Symmetric Encryption
Model of Symmetric
Cryptosystem
 Cryptographic
Systems
• Characterized along three independent
dimensions:
The type of
operations used The way in which
The number of
for transforming the plaintext is
keys used
plaintext to processed
ciphertext
Symmetric,
single-key,
Substitution secret-key, Block cipher
conventional
encryption

Asymmetric,
two-key, or
Transposition Stream cipher
public-key
encryption
Brute-force Cryptanalysis
attack • Attack relies on
• Attacker tries the nature of
the algorithm
every possible
plus some
key on a piece
knowledge of
of ciphertext
the general
until an
characteristics
intelligible
of the plaintext
translation into
• Attack exploits
plaintext is
obtained the
• On average, characteristics
of the
half of all
algorithm to
possible keys
attempt to
must be tried
deduce a
to achieve
specific
success
plaintext or to
deduce the key
being used
Brute-Force Attack
Cryptanalysis and
Table 2.1
Types of
Attacks
on
Encrypted
Messages
 Encryption Scheme
Security
• Unconditionally secure
• No matter how much time an opponent
has, it is impossible for him or her to
decrypt the ciphertext simply because
the required information is not there

• Computationally secure
• The cost of breaking the cipher exceeds
the value of the encrypted information
• The time required to break the cipher
exceeds the useful lifetime of the
information
 Brute-Force Attack
Involves trying every possible key until an
intelligible translation of the ciphertext into
plaintext is obtained

On average, half of all possible keys must be

tried to achieve success

To supplement the brute-force approach,

some degree of knowledge about the
expected plaintext is needed, and some
means of automatically distinguishing
plaintext from garble is also needed
 Substitution
Technique
• Is one in which the letters of plaintext
are replaced by other letters or by
numbers or symbols

• If the plaintext is viewed as a sequence

of bits, then substitution involves
replacing plaintext bit patterns with
ciphertext bit patterns
 Caesar Cipher
• Simplest and earliest known use of a substitution
cipher
• Used by Julius Caesar

• Involves replacing each letter of the alphabet

with the letter standing three places further down
the alphabet
• Alphabet is wrapped around so that the letter
following Z is A

plain: meet me after the toga party

cipher: PHHW PH DIWHU WKH WRJD SDUWB

 Caesar Cipher
Algorithm
• Can define transformation as:
a b c d e f g h i j k l m n o p q r s t u v w x y z
D E F G H I J K L M N O P Q R S T U V W X Y Z A B C

• Mathematically give each letter a number

a b c d e f g h i j k l m n o p q r s t u v w x y z
0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25

• Algorithm can be expressed as:

c = E(3, p) = (p + 3) mod (26)

• A shift may be of any amount, so that the general Caesar

algorithm is:
C = E(k , p ) = (p + k ) mod 26
• Where k takes on a value in the range 1 to 25; the
decryption algorithm is simply:

p = D(k , C ) = (C - k ) mod 26
 Brute-Force
Cryptanalysis
of Caesar
Cipher

(This chart can be found on

page 35 in the textbook)
Sample of Compressed
Text
 Monoalphabetic
Cipher
• Permutation
• Of a finite set of elements S is an ordered
sequence of all the elements of S , with each
element appearing exactly once

• If the “cipher” line can be any permutation

of the 26 alphabetic characters, then there
are 26! or greater than 4 x 1026 possible keys
• This is 10 orders of magnitude greater than the
key space for DES
• Approach is referred to as a monoalphabetic
substitution cipher because a single cipher
alphabet is used per message
 Monoalphabetic
Ciphers
• Easy to break because they reflect the
frequency data of the original alphabet

• Countermeasure is to provide multiple

substitutes (homophones) for a single letter

• Digram
• Two-letter combination
• Most common is th

• Trigram
• Three-letter combination
• Most frequent is the
 Playfair Cipher
• Best-known multiple-letter encryption cipher

• Treats digrams in the plaintext as single units

and translates these units into ciphertext
digrams
• Based on the use of a 5 x 5 matrix of letters
constructed using a keyword
• Invented by British scientist Sir Charles
Wheatstone in 1854
• Used as the standard field system by the
British Army in World War I and the U.S. Army
and other Allied forces during World War II
 Playfair Key Matrix
• Fill in letters of keyword (minus
duplicates) from left to right and from
top to bottom, then fill in the
remainder of the matrix with the
remaining letters in alphabetic order

• Using the keyword MONARCHY:

M O N A R
C H Y B D
E F G I/J K
L P Q S T
U V W X Z
 Hill Cipher
• Developed by the mathematician Lester
Hill in 1929
• Strength is that it completely hides single-
letter frequencies
• The use of a larger matrix hides more
frequency information
• A 3 x 3 Hill cipher hides not only single-
letter but also two-letter frequency
information

• Strong against a ciphertext-only attack but

easily broken with a known plaintext attack
 Polyalphabetic
Ciphers
• Polyalphabetic substitution cipher
• Improves on the simple monoalphabetic
technique by using different
monoalphabetic substitutions as one
proceeds through the plaintext message

All these techniques have the following

features in common:
• A set of related monoalphabetic
substitution rules is used
• A key determines which particular
rule is chosen for a given
transformation
 Vigenère Cipher
• Best known and one of the simplest
polyalphabetic substitution ciphers

• In this scheme the set of related

monoalphabetic substitution rules
consists of the 26 Caesar ciphers with
shifts of 0 through 25

• Each cipher is denoted by a key letter

which is the ciphertext letter that
substitutes for the plaintext letter a
 Example of Vigenère
Cipher
• To encrypt a message, a key is needed that is as
long as the message
• Usually, the key is a repeating keyword

• For example, if the keyword is deceptive, the

message “we are discovered save yourself” is
encrypted as:

key: deceptivedeceptivedeceptive
plaintext: wearediscoveredsaveyourself
ciphertext: ZICVTWQNGRZGVTWAVZHCQYGLMGJ
Vigenère Autokey System
• A keyword is concatenated with the plaintext
itself to provide a running key

• Example:
key: deceptivewearediscoveredsav
plaintext: wearediscoveredsaveyourself
ciphertext: ZICVTWQNGKZEIIGASXSTSLVVWLA

• Even this scheme is vulnerable to

cryptanalysis
• Because the key and the plaintext share the
same frequency distribution of letters, a
statistical technique can be applied
Vernam Cipher
 One-Time Pad
• Improvement to Vernam cipher proposed by an Army
Signal Corp officer, Joseph Mauborgne
• Use a random key that is as long as the message so that
the key need not be repeated
• Key is used to encrypt and decrypt a single message and
then is discarded
• Each new message requires a new key of the same length
as the new message
• Scheme is unbreakable
• Produces random output that bears no statistical
relationship to the plaintext
• Because the ciphertext contains no information whatsoever
about the plaintext, there is simply no way to break the
code
 Difficulties
• The one-time pad offers complete security but, in
practice, has two fundamental difficulties:
• There is the practical problem of making large quantities
of random keys
• Any heavily used system might require millions of random
characters on a regular basis
• Mammoth key distribution problem
• For every message to be sent, a key of equal length is
needed by both sender and receiver

• Because of these difficulties, the one-time pad is of

limited utility
• Useful primarily for low-bandwidth channels requiring
very high security

• The one-time pad is the only cryptosystem that exhibits

perfect secrecy (see Appendix F)
 Rail Fence Cipher
• Simplest transposition cipher

• Plaintext is written down as a sequence of

diagonals and then read off as a sequence of
rows

• To encipher the message “meet me after the

toga party” with a rail fence of depth 2, we
would write:
mematrhtgpry
etefeteoaat
Encrypted message is:
MEMATRHTGPRYETEFETEOAAT
Row Transposition Cipher
• Is a more complex transposition

• Write the message in a rectangle, row by row, and

read the message off, column by column, but
permute the order of the columns
• The order of the columns then becomes the key to
the algorithm
Key: 4 3 1 2 5 6 7
Plaintext: atta c kp
ostpone
dunt i l t
w o a mx y z
Ciphertext:
TTNAAPTMTSUOAODWCOIXKNLYPETZ
Rotor Machines
Steganography
 • Character marking
• Selected letters of printed or
typewritten text are over-
Other written in pencil
• The marks are ordinarily not
Steganograph visible unless the paper is
held at an angle to bright
y Techniques light
• Invisible ink
• A number of substances can
be used for writing but leave
no visible trace until heat or
some chemical is applied to
the paper
• Pin punctures
• Small pin punctures on
selected letters are ordinarily
not visible unless the paper is
held up in front of a light
• Typewriter correction
ribbon
• Used between lines typed
with a black ribbon, the
 Summary
• Symmetric Cipher • Substitution
Model techniques
• Cryptography • Caesar cipher
• Cryptanalysis and • Monoalphabetic
Brute-Force Attack ciphers
• Playfair cipher
• Transposition
• Hill cipher
techniques
• Polyalphabetic
• Rotor machines ciphers
• One-time pad

• Steganography