Cryptography and

Network Security
Chapter 2
Fifth 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
 or conventional / private-key / single-key
 sender and recipient share a common key
 all classical encryption algorithms are
private-key
 was only type prior to invention of public-
key in 1970’s
 and by far most widely used (still)
 is significantly faster than public-key crypto
 Some Basic Terminology
 plaintext - original message, normal text
 ciphertext - coded message, text after encryption
 cipher - algorithm for transforming plaintext to ciphertext
 Secret key - info used in cipher known only to
sender/receiver. Input to the encryption algorithem
 encipher (encrypt) - converting plaintext to ciphertext
 decipher (decrypt) - recovering plaintext from ciphertext
 cryptography - study of encryption principles/methods
 cryptanalysis (codebreaking) - study of principles/
methods of deciphering ciphertext without knowing key
 cryptology - field of both cryptography and cryptanalysis
Symmetric Cipher Model
 Requirements
 two requirements for secure use of symmetric
encryption:
 a strong encryption algorithm
 a secret key known only to sender / receiver
 mathematically have:
Y = E(K, X) = EK(X) = {X}K
X = D(K, Y) = DK(Y)
 assume encryption algorithm is known
 Kerckhoff’s Principle: security in secrecy of key alone,
not in obscurity of the encryption algorithm
 implies a secure channel to distribute key
 Central problem in symmetric cryptography
 Cryptography
 can characterize cryptographic system by:
 type of encryption operations used
• Substitution (putting one element into another)
• Transposition (elements in the plaintext is rearranged)
• Product (multiple stages of substitution and transposition)
 number of keys used
• single-key or private (Symmetric )
• two-key or public (Asymmetric)
 way in which plaintext is processed
• block
• stream
 Cryptanalysis
 objective to recover key not just message
 general approaches:
 cryptanalytic attack
 brute-force attack
 if either succeed all key use compromised
 Cryptanalytic Attacks
 ciphertext only
 only know algorithm & ciphertext, is statistical,
can identify plaintext
 known plaintext
 know/suspect plaintext & ciphertext
 chosen plaintext
 select plaintext and obtain ciphertext
 chosen ciphertext
 select ciphertext and obtain plaintext
 chosen text
 select plaintext or ciphertext to en/decrypt
 Cipher Strength
 unconditional security
 no matter how much computer power or time
is available, the cipher cannot be broken
since the ciphertext provides insufficient
information to uniquely determine the
corresponding plaintext
 computational security
 given limited computing resources (e.g. time
needed for calculations is greater than age of
universe), the cipher cannot be broken
 Brute Force Search
 always possible to simply try every key
 most basic attack, exponential in key length
 assume either know / recognise plaintext
Key Size (bits) Number of Alternative Time required at 1 Time required at 106
Keys decryption/µs decryptions/µs

32 232 = 4.3  109 231 µs = 35.8 minutes 2.15 milliseconds

56 256 = 7.2  1016 255 µs = 1142 years 10.01 hours

128 2128 = 3.4  1038 2127 µs = 5.4  1024 years 5.4  1018 years

168 2168 = 3.7  1050 2167 µs = 5.9  1036 years 5.9  1030 years

26 characters 26! = 4  1026 2  1026 µs = 6.4  1012 years 6.4  106 years
(permutation)

 Data Encryption Algorithm (DES) – uses 56 bit key size

 Triple DES – uses 168 bit key size
 Advance Encryption Standard (AES) - uses 128 bit key Size
 Classical Substitution
Ciphers
 where letters of plaintext are replaced by
other letters or by numbers or symbols
 or if plaintext is viewed as a sequence of
bits, then substitution involves replacing
plaintext bit patterns with ciphertext bit
patterns
 Caesar Cipher
 earliest known substitution cipher
 by Julius Caesar
 first attested use in military affairs
 replaces each letter by 3rd letter on
 example:
meet me after the toga party
PHHW PH DIWHU WKH WRJD SDUWB
 Caesar Cipher
 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 =
IN
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 =
OUT

 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

 then have Caesar (rotation) cipher as:

c = E(k, p) = (p + k) mod (26)
p = D(k, c) = (c – k) mod (26)
 Cryptanalysis of Caesar
Cipher
 only have 26 possible ciphers
 A maps to A,B,..Z
 could simply try each in turn
 a brute force search
 given ciphertext, just try all shifts of letters
 do need to recognize when have plaintext
 eg. break ciphertext "GCUA VQ DTGCM"
 Affine Cipher
broaden to include multiplication
can define affine transformation as:
c = E(k, p) = (ap + b) mod (26)
p = D(k, c) = (a-1(c – b)) mod (26)
key k=(a,b)
a must be relatively prime to 26
so there exists unique inverse a-1
 Affine Cipher - Example
 example k=(17,3):
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 = IN
D U L C T K B S J A R I Z Q H Y P G X O F W N E V
M = OUT
 example:
meet me after the toga party
ZTTO ZT DKOTG OST OHBD YDGOV
 Now how many keys are there?
 12 x 26 = 312
 Still can be brute force attacked!
 Monoalphabetic Cipher
 rather than just shifting the alphabet
 could shuffle (permute) the letters arbitrarily
 each plaintext letter maps to a different random
ciphertext letter
 hence key is 26 letters long

Plain: abcdefghijklmnopqrstuvwxyz
Cipher: DKVQFIBJWPESCXHTMYAUOLRGZN

Plaintext: ifwewishtoreplaceletters
Ciphertext: WIRFRWAJUHYFTSDVFSFUUFYA
 Monoalphabetic Cipher
Security
 key size is now 25 characters…
 now have a total of 26! = 4 x 1026 keys
 with so many keys, might think is secure
 but would be !!!WRONG!!!
 problem is language characteristics
 Language Redundancy and
Cryptanalysis
 human languages are redundant
 e.g., "th lrd s m shphrd shll nt wnt"
 letters are not equally commonly used
 in English E is by far the most common letter
 followed by T,R,N,I,O,A,S
 other letters like Z,J,K,Q,X are fairly rare
 have tables of single, double & triple letter
frequencies for various languages
English Letter Frequencies
 English Letter Frequencies
Sorted Relative Frequencies

14.000
12.000
10.000
8.000
6.000
4.000
2.000
0.000
E T A O I N S H R D L C U MW F G Y P B V K J X Q Z
What kind of cipher is this?
English Letter Frequencies

14.000
12.000
10.000
8.000
6.000
4.000
2.000
0.000
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

Frequences for Cipher-0

14.000
12.000
10.000
8.000
6.000
4.000
2.000
0.000
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
What kind of cipher is this?
English Letter Frequencies

14.000
12.000
10.000
8.000
6.000
4.000
2.000
0.000
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

Frequencies for Cipher-1

14.000
12.000
10.000
8.000
6.000
4.000
2.000
0.000
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
 Use in Cryptanalysis
 key concept - monoalphabetic substitution
ciphers do not change relative letter frequencies
 discovered by Arabian scientists in 9th century
 calculate letter frequencies for ciphertext
 compare counts/plots against known values
 if caesar cipher look for common peaks/troughs
 peaks at: A-E-I triple, N-O pair, R-S-T triple
 troughs at: J-K, U-V-W-X-Y-Z
 for monoalphabetic must identify each letter
 tables of common double/triple letters help
(digrams and trigrams)
 amount of ciphertext is important – statistics!
 Example Cryptanalysis
 given ciphertext:
UZQSOVUOHXMOPVGPOZPEVSGZWSZOPFPESXUDBMETSXAIZ
VUEPHZHMDZSHZOWSFPAPPDTSVPQUZWYMXUZUHSX
EPYEPOPDZSZUFPOMBZWPFUPZHMDJUDTMOHMQ

 count relative letter frequencies (see text)

 Example Cryptanalysis
 given ciphertext:
UZQSOVUOHXMOPVGPOZPEVSGZWSZOPFPESXUDBMETSXAIZ
VUEPHZHMDZSHZOWSFPAPPDTSVPQUZWYMXUZUHSX
EPYEPOPDZSZUFPOMBZWPFUPZHMDJUDTMOHMQ
 guess P & Z are e and t
 guess ZW is th and hence ZWP is “the”
 proceeding with trial and error finally get:
it was disclosed yesterday that several informal
but
direct contacts have been made with political
representatives of the viet cong in moscow
 Playfair Cipher
 not even the large number of keys in a
monoalphabetic cipher provides security
 one approach to improving security was to
encrypt multiple letters
 the Playfair Cipher is an example
 invented by Charles Wheatstone in 1854,
but named after his friend Baron Playfair
 Playfair Key Matrix
 a 5X5 matrix of letters based on a keyword
 fill in letters of keyword (sans duplicates)
 fill rest of matrix with other letters
 eg. 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
 Encrypting and Decrypting
 plaintext is encrypted two letters at a time
1. if a pair is a repeated letter, insert filler like 'X’
2. if both letters fall in the same row, replace
each with letter to right (wrapping back to start
from end)
3. if both letters fall in the same column, replace
each with the letter below it (wrapping to top
from bottom)
4. otherwise each letter is replaced by the letter
in the same row and in the column of the other
letter of the pair
 Playfair Example
 Message = Move forward
 Plaintext = mo ve fo rw ar dx
 Here x is just a filler, message is padded and segmented

 Ciphertext = ON UF PH NZ RM BZ
 mo -> ON; ve -> UF; fo -> PH, etc.

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
 Security of Playfair Cipher
 security much improved over monoalphabetic
 since have 26 x 26 = 676 digrams
 would need a 676 entry frequency table to
analyse (versus 26 for a monoalphabetic)
 and correspondingly more ciphertext
 was widely used for many years
 eg. by US & British military in WW1
 it can be broken, given a few hundred letters
 since still has much of plaintext structure
 Polyalphabetic Ciphers
 polyalphabetic substitution ciphers
 improve security using multiple cipher alphabets
 make cryptanalysis harder with more alphabets
to guess and flatter frequency distribution
 use a key to select which alphabet is used for
each letter of the message
 use each alphabet in turn
 repeat from start after end of key is reached
 Vigenère Cipher
 simplest polyalphabetic substitution cipher
 effectively multiple caesar ciphers
 key is multiple letters long K = k1 k2 ... kd
 ith letter specifies ith alphabet to use
 use each alphabet in turn
 repeat from start after d letters in message
 decryption simply works in reverse
 Example of Vigenère Cipher
 write the plaintext out
 write the keyword repeated above it
 If the key is d plain text is w encryption is z
 If the key is e plain text is e encryption is i
 use each key letter as a caesar cipher key
 encrypt the corresponding plaintext letter
 eg using keyword deceptive
key: deceptivedeceptivedeceptive
plaintext: wearediscoveredsaveyourself
ciphertext:ZICVTWQNGRZGVTWAVZHCQYGLMGJ
 Security of Vigenère Ciphers
 have multiple ciphertext letters for each
plaintext letter
 hence letter frequencies are obscured
 but not totally lost
 start with letter frequencies
 see if it looks monoalphabetic or not
 if not, then need to determine number of
alphabets, since then can attack each
 Frequencies After Polyalphabetic
Encryption
Letter Relative Frequency

14.000
12.000
equiprobable
10.000
unencrypted
8.000
two keys
6.000
four keys
4.000
eight keys
2.000
0.000
Frequencies After Polyalphabetic
Encryption
Sorted relative frequencies

14
12
10 Equiprobible
Unencrypted/1 key
8
two keys
6
four keys
4
eight keys
2
0
1 4 7 10 13 16 19 22 25
 Kasiski Method
 method developed by Babbage / Kasiski
 repetitions in ciphertext give clues to period
 so find same plaintext a multiple of key length
apart
 which results in the same ciphertext
 of course, could also be random fluke
 e.g. repeated “VTW” in previous example
 distance of 9 suggests key size of 3 or 9
 then attack each monoalphabetic cipher
individually using same techniques as before
 Example of Kasiski Attack
 Find repeated ciphertext trigrams (e.g., VTW)
 May be result of same key sequence and same
plaintext sequence (or not)
 Find distance(s)
 Common factors are likely key lengths

key: deceptivedeceptivedeceptive
plaintext: wearediscoveredsaveyourself
ciphertext:ZICVTWQNGRZGVTWAVZHCQYGLMGJ
 Autokey Cipher
 A key word is concatenated with the plain text
itself to provide a running key.
 ideally want a key as long as the message
 Vigenère proposed the autokey cipher
 with keyword is prefixed to message as key
 knowing keyword can recover the first few letters
 use these in turn on the rest of the message
 but still have frequency characteristics to attack
 eg. given key deceptive
key: deceptivewearediscoveredsav
plaintext: wearediscoveredsaveyourself
ciphertext:ZICVTWQNGKZEIIGASXSTSLVVWLA
 Vernam Cipher
 Work with binary data rather than latters
 Make exclusive or with the data
 ultimate defense is to use a key as long as the
plaintext
 with no statistical relationship to it
 invented by AT&T engineer Gilbert Vernam in
1918
 specified in U.S. Patent 1,310,719, issued July
22, 1919
 originally proposed using a very long but
eventually repeating key
 used electromechanical relays
 One-Time Pad
 The length of the key is equal to the length of the
massage. The key is not repeated
 The new massage will have the new key
 if a truly random key as long as the message is
used, the cipher will be secure
 called a One-Time pad (OTP)
 is unbreakable since ciphertext bears no
statistical relationship to the plaintext
 since for any plaintext & any ciphertext there
exists a key mapping one to other
 can only use the key once though
 problems in generation & safe distribution of key
 Transposition Ciphers
 now consider classical transposition or
permutation ciphers
 these hide the message by rearranging
the letter order
 without altering the actual letters used
 can recognise these since have the same
frequency distribution as the original text
 Rail Fence cipher
 write message letters out diagonally over a
number of rows
 then read off cipher row by row
 eg. write message out as:

 Meet me after toga party

m e m a t r h t g p r y
e t e f e t e o a a t
 giving ciphertext
MEMATRHTGPRYETEFETEOAAT
 Row Transposition Ciphers
 is a more complex transposition
 write letters of message out in rows over a
specified number of columns
 then reorder the columns according to
some key before reading off the rows
 Take the column labelled 1, then labelled
2 and so on
Key: 4312567
Column Out 4 3 1 2 5 6 7
Plaintext: a t t a c k p
o s t p o n e
d u n t i l t
w o a m x y z
Ciphertext: TTNAAPTMTSUOAODWCOIXKNLYPETZ
 Block Transposition Ciphers
 arbitrary block transposition may be used
 specify permutation on block
 repeat for each block of plaintext
Key: 8342067951
Plaintext: attackpost poneduntil twoamxyzab

Ciphertext: CTATTSKPAO DLEONIDUPT MBAWOAXYTZ

 Product Ciphers
 ciphers using substitutions or transpositions are
not secure because of language characteristics
 hence consider using several ciphers in
succession to make harder, but:
 two substitutions make a more complex substitution
 two transpositions make more complex transposition
 but a substitution followed by a transposition makes a
new much harder cipher
 this is bridge from classical to modern ciphers
 Rotor Machines
 before modern ciphers, rotor machines were most common
complex ciphers in use
 widely used in WW2
 German Enigma, Allied Hagelin, Japanese Purple
 implemented a very complex, varying substitution cipher
 used a series of cylinders, each giving one substitution, which
rotated and changed after each letter was encrypted
 with 3 cylinders have 263=17576 alphabets
 The cylinder closest to the operator rotates one pin position with
each keystroke
 For every complete rotation of first cylinder the second cylinder
rotates one pin
 For every complete rotation of second cylinder the third cylinder
rotates one pin
Hagelin Rotor Machine
Rotor Machine Principles
 Rotor Ciphers
 Each rotor implements some permutation
between its input and output contacts
 Rotors turn like an odometer on each key
stroke (rotating input and output contacts)
 Key is the sequence of rotors and their
initial positions
 Steganography
 an alternative to encryption
 hides existence of message
 using only a subset of letters/words in a longer
message marked in some way
 using invisible ink
 hiding in LSB in graphic image or sound file
 hide in “noise”
 has drawbacks
 high overhead to hide relatively few info bits
 advantage is can obscure encryption use
 Summary
 have considered:
 classical cipher techniques and terminology
 monoalphabetic substitution ciphers
 cryptanalysis using letter frequencies
 Playfair cipher
 polyalphabetic ciphers
 transposition ciphers
 product ciphers and rotor machines
 steganography