Chapter No.

2
Classical Encryption
Techniques
 Cryptographic Tools (outlines)

 Cryptographicalgorithms are important

element in security services
 The practice and study of hiding information
 Review of various types of elements
 symmetric encryption
 public-key (asymmetric) encryption
 digital signatures and key management
 secure hash functions
 example is use to encrypt stored data
 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
 Some Basic Terminology
 plaintext - original message
 ciphertext - coded message
 cipher - algorithm for transforming plaintext to ciphertext
 key - info used in cipher known only to sender/receiver
 encipher (encrypt) - converting plaintext to ciphertext
 decipher (decrypt) - recovering ciphertext from plaintext
 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 = EK(X)
X = DK(Y)
 assume encryption algorithm is known
 implies a secure channel to distribute key
 Cryptography
 Cryptographicsystems can be
characterized along these three
independent dimensions:
 type of encryption operations used
• substitution / transposition / product
 number of keys used
• single-key or private / two-key or public
 way in which plaintext is processed
• block / stream
 Blockcipher: A block cipher processes the input
one block of elements at a time, producing an
output block for each input block.
 A symmetric encryption algorithm in which a block
of plaintext bits (typically 64 or 128) is transformed
as a whole into a ciphertext block of the same
length.
 Stream cipher: A stream cipher processes the
input elements continuously, producing output
one element at a time, as it goes along.
 A symmetric encryption algorithm in which
ciphertext output is produced bit-by-bit or byte-by-
byte from a stream of plaintext input.
 Cryptanalysis
 Objectiveto recover key not just message
 General approaches:
 cryptanalytic attack
 brute-force attack
 Attacking Symmetric
Encryption
 cryptanalysis
 rely on nature of the algorithm
 plus some knowledge of plaintext
characteristics
 even some sample plaintext-ciphertext pairs
 exploits characteristics of algorithm to deduce
specific plaintext or key
 brute-force attack
 try all possible keys on some ciphertext until
get an intelligible translation into plaintext
 More Definitions
 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 (eg 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, proportional to key size
 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)
 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
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

 First we need to convert the alphabets

into num.
 Encryptionof a letter “p” by letter “K” can be
described as:
c = E(k , p) = (p + k) mod (26)

 Similarly decryption can be performed as:

p = D(k , c) = (c – k) mod (26)

Example: …….
Use the key of any shift, if the resultant value is
larger than 26 than subtract 26…
Reverse the process during decryption.
 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"
 The Caesar Cipher is clearly unsuitable for
modern use!

 Identify at least three cryptographic

weaknesses that result in the Caesar
Cipher being regarded as insecure.
 Monoalphabetic Cipher
 rather than just shifting the alphabet
 could shuffle (jumble) 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
 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
 eg “this is pakistan"
 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
 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, NO pair, RST triple
 troughs at: JK, X-Z
 for monoalphabetic must identify each letter
 tables of common double/triple letters help
 Example Cryptanalysis
 given ciphertext:
UZQSOVUOHXMOPVGPOZPEVSGZWSZOPFPESXUDBMETSXAIZ
VUEPHZHMDZSHZOWSFPAPPDTSVPQUZWYMXUZUHSX
EPYEPOPDZSZUFPOMBZWPFUPZHMDJUDTMOHMQ
 count relative letter frequencies (see text)
 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 (minus 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 (again 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
 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 (verses 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
 use each key letter as a caesar cipher key
 encrypt the corresponding plaintext letter
 eg using keyword deceptive
key: deceptivedeceptivedeceptive
plaintext: wearediscoveredsaveyourself
ciphertext:ZICVTWQNGRZGVTWAVZHCQYGLMGJ
 Presentation Outline
 Vigenere cipher.
 Attacks on Vigenere : Kasisky
Test

37
 Towards the Polyalphabetic
Substitution Ciphers
 Mainweaknesses of monoalphabetic
substitution ciphers
 In ciphertext, different letters have different
frequency
• each letter in the ciphertext corresponds to only
one letter in the plaintext letter
 Ideafor a stronger cipher (1460’s by
Alberti)
 Use more than one cipher alphabet, and
switch between them when encrypting 38
different letters
 The Vigenère Cipher
Treat letters as numbers: [A=0, B=1, C=2, …, Z=25]
Number Theory Notation: Zn= {0, 1, …, n-1}
Definition:
Given m, a positive integer, P = C = (Z26)n, and K =
(k1, k2, … , km) a key, we define:
Encryption:
ek(p1, p2… pm) = (p1+k1, p2+k2…pm+km) (mod 26)
Decryption:
dk(c1, c2… cm) = (c1-k1, c2-k2 … cm- km) (mod 26)
Example:
Plaintext: C R Y P T O G R A P H Y
Key: LUCKLUC KLUCK
Ciphertext: N L A Z E I I B L J J I
39
 Security of Vigenere Cipher
 Vigenere masks the frequency with which a
character appears in a language: one letter in
the ciphertext corresponds to multiple letters
in the plaintext. Makes the use of frequency
analysis more difficult.
 Any message encrypted
by a Vigenere cipher is a
collection of as many shift ciphers as there
are letters in the key.

40
 Vigenere Cipher:
Cryptanalysis
 Find the length of the key.
 Divide the message into
that many simple
substitution encryptions.
 Solve the resulting simple
substitutions.
 how?

41
How to Find the Key Length?
 For Vigenere, as the length of the keyword
increases, the letter frequency shows less
English-like characteristics and becomes
more random.
 Two methods to find the key
length:
 Kasisky test
 Index of coincidence
(Friedman)

42
 Kasisky Test
 The Kasiski examination, also called the
Kasiski test, takes advantage of the fact
that repeated words may, by chance,
sometimes be encrypted using the same
key letters, leading to repeated groups in
the ciphertext .
 For example, Consider the following
encryption using the keyword ABCD:

43
 Example of the Kasisky Test
 Key:
ABCDABCDABCDABCDABCDABCDABC
D Plaintext:
CRYPTOISSHORTFORCRYPTOGRAPH
Y Ciphertext:
CSASTPKVSIQUTGQUCSASTPIUAQJB

44
 Kasisky Test
 There is an easily seen repetition in the
ciphertext, and the Kasiski test will be
effective.
 Here the distance between the repetitions
of CSASTP is 16.
 .Assuming that the repeated segments
represent the same plaintext segments,
this implies that the key is 16, 8, 4, 2, or 1
characters long.
45
 Kasisky Test
 The following ciphertext has two segments
that are repeated:
 Ciphertext:
VHVSSPQUCEMRVBVBBBVHVSURQGI
BDUGRNICJQUCERVUAXSSR

46
 Kasisky Test
 The distance between the repetitions
of VHVS is 18.
 Assuming that the repeated segments
represent the same plaintext segments,
this implies that the key is 18, 9, 6, 3, 2, or
1 characters long.
 The distance between the repetitions
of QUCE is 30 characters.
47
 Kasisky Test
 This means that the key length could be
30, 15, 10, 6, 5, 3, 2, or 1 characters long.
 By taking the intersection of these sets
one could safely conclude that the most
likely key length is 6, since 3, 2, and 1 are
unrealistically short.

48
 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 look monoalphabetic or not
 ifnot, then need to determine number of
alphabets (length of keyword), since then
can attach each
 Kasiski Method
 method developed by Babbage / Kasiski
 repetitions in ciphertext give clues to period
 so find same plaintext an exact period apart
 which results in the same ciphertext
 of course, could also be random fluke
 eg repeated “VTW” in previous example
 suggests size of 3 or 9
 then attack each monoalphabetic cipher
individually using same techniques as before
 Autokey Cipher
 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
 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.
 The ultimate defense against such a
cryptanalysis is to choose a keyword that is
as long as the plaintext and has no statistical
relationship to it. Such a system was
introduced by an AT&T engineer named
Gilbert Vernam in 1918. His system works on
binary data rather than letters. The system
can be expressed concisely as follows:
 Thus, the ciphertext
is generated by
performing the bitwise
XOR of the plaintext
and the key.
 Because of the
properties of the XOR, decryption simply
involves the same bitwise operation:
 One-Time Pad
 if a truly random key as long as the message is
used, the cipher will be secure
 Each new message requires a new key of the
same length as the new message
 called a One-Time pad
 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
 TRANSPOSITION CIPHER
 In the transposition technique the positions of
letters/numbers/symbols in plain text is changed with one
another.
1 2 3 4 5 6 4 2 1 6 3 5
M E E T M E T E M E E M
A F T E R P E F A P T R
A R T Y Y R A T

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 Transposition cipher techniques

1. RailFence Cipher
2. Columnar Transposition
 Simple Columnar Transposition
 Double Columnar Transposition
 1. Rail Fence Cipher

 In this method plain text is written downwards on “rails of

fence “ , starting a new column when bottom is reached.
 Algorithm:
1. First write down plain text message as a sequence of
diagonals.
2. Read the plain text written in first step as a sequence of rows.
 1. Rail Fence Cipher

Example:
Plain text: come home tomorrow

Cipher text: cmhmtmrooeoeoorw

 1. Simple Columnar Transposition

 In this method the message is written in rows of fixed

length and then read out column by column
 Column are selected in some in some scrambled order.
 The number of columns are defined by the length of
key.
 Algorithm:
1. Write the plain text message row by row in a rectangle
of predefined size.(length of key)
2. Read the message column by column according t the
selected order thus obtained message is a cipher text.
 1. Simple Columnar Transposition

Key: ZEBRAS
plain text: welcome home
Order : 6 3 2 4 1 5

Cipher text: MLOEHCMWEOE

 2.Double Columnar Transposition

 Single columnar transposition can be attack by guessing possible

column lengths.
 Therefore to make it stronger double transposition is used.
 This is simple columnar transposition technique applied twice.
 Here same key can be used for transposition or two different keys
can be used.
 2.Double Columnar Transposition

 First apply simple columnar transposition

Key: ZEBRAS
plain text: welcome home
Order : 6 3 2 4 1 5

Cipher text: MLOEHCMWEOE

 2.Double Columnar Transposition

Cipher text 1: MLOEHCMWEOE

Order : 6 3 2 4 1 5

Final Cipher Text: COELWEOMMHE

 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:
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
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
Key: 3 4 2 1 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
 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
Hagelin Rotor Machine
Rotor Machine Principles
 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
 has drawbacks
 high overhead to hide relatively few info bits
 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
 stenography