6/27/2022

Classical Encryption Techniques

Instructor: Nguyen Tan Cam, Ph.D.

LEARNING OBJECTIVES
• After studying this chapter, you should be able to:
• Present an overview of the main concepts of symmetric cryptography.
• Explain the difference between cryptanalysis and brute-force attack.
• Understand the operation of a monoalphabetic substitution cipher.
• Understand the operation of a polyalphabetic cipher.
• Present an overview of the Hill cipher.
• Describe the operation of a rotor machine

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Introduction
• 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.
• It remains by far the most widely used of the two types of encryption.
• In lesson, we begin with a look at a general model for the symmetric
encryption process;
• This will enable us to understand the context within which the
algorithms are used.
• Next, we examine a variety of algorithms in use before the computer
era. Finally, we look briefly at a different approach known as
steganography.

Some terms
Plaintext • An original message

Ciphertext • The coded message

Enciphering / encryption • The process of converting from plaintext to ciphertext

Deciphering / decryption • Restoring the plaintext from the ciphertext

Cryptography • Study of encryption principles/methods

• Techniques used for deciphering a message without any knowledge of the

Cryptanalysis enciphering details fall into the area of cryptanalysis

Cryptology • Field of both cryptography and cryptanalysis

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Symmetric Cipher Model

• A symmetric encryption scheme has five ingredients: Plaintext,
Encryption algorithm, Secret key, Ciphertext, Decryption Algorithm.

Model of Symmetric Cryptosystem

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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
• characterize cryptographic system by: substitution

type of
encryption transposition
operations used

product

single-key
number of keys
used
private / two-key
or public

block
way in which
plaintext is
processed
stream

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Cryptanalysis
• objective to recover key not just message
• general approaches:
• cryptanalytic attack
• brute-force attack

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Cryptanalytic Attacks
• ciphertext only
• only know algorithm & ciphertext, is statistical, know or 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

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

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Brute Force Search

• always possible to simply try every key
• most basic attack, proportional to key size
• assume either know / recognise plaintext

Number of Alternative Time required at 1 Time required at 106

Key Size (bits)
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

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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
• Mathematically, give each letter a number

• The key is a number from 0 to 25

• Caesar cipher can now be given as
Calculation Negative MOD
Modula always return non-negative number:
Calculate the following mode:
E.g., (-57) mod 21
= (-36) mod 21
= (-15) mod 21
= (6) mod 21
=6

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Attacking Caesar
• Caesar can be broken if we only know one pair (plain letter, encrypted
letter)
• The difference between them is the key
• Caesar can be broken even if we only have the encrypted text and no
knowledge of the plaintext
• Brute-force attack is easy: there are only 25 keys possible
• Try all 25 keys and check to see which key gives an intelligible message

Attacking Caesar

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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"

An example with Python

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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

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Language Redundancy and Cryptanalysis

• human languages are redundant
• eg "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

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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

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Playfair Cipher
• The Playfair Cipher is an example of multiple-letter encryption
• Invented by Sir Charles Wheatstone in 1854, but named after his
friend Baron Playfair who championed the cipher at the British
foreign office
• Based on the use of a 5x5 matrix in which the letters of the alphabet
are written (I is considered the same as J)
• This is called key matrix

Playfair Cipher
• A 5X5 matrix of letters based on a keyword
• Fill in letters of keyword (no duplicates)
• Left to right, top to bottom
• Fill the rest of matrix with the other letters in alphabetic order
• E.g. using the keyword MONARCHY, we obtain the following matrix

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Encrypting and decrypting with Playfair

• The plaintext is encrypted two letters at a time
• Break the plaintext into pairs of two consecutive letters
• If a pair is a repeated letter, insert a filler like 'X‘ in the plaintext, eg. "balloon" is treated
as "ba lx lo on"
• Ex: Keyword: PLAYFAIR EXAM
• Plain text: HIDEEXTHEGOL -> HI DE EX TH EG OL

Vigenère Cipher
• Proposed by Giovan Batista Belaso (1553) and reinvented by Blaise de Vigenère
(1586), called “le chiffre indéchiffrable” for 300 years
• Effectively multiple Caesar ciphers
• Key is a word

• Encryption
• Read one letter t from the plaintext and one letter k from the key-word
• t is encrypted according to the Caesar cipher with key k
• for the next plain-letter, use the next letter from the key-word
• When the key word is finished, start the reading of the key from the beginning
• In other words: ci=(pi+ki mod m) mod 26
• Decryption works in reverse
• Example: key is “bcde”; “testing” is encrypted as “ugvxjpj”
• Note that the two ‘t’ are encrypted by different letters: ‘u’ and ‘x’
• The two ‘j’ in the cryptotext come from different plain letters: ‘i’ and ‘j’

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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

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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

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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

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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

Vigenère Cipher
• Proposed by Giovan Batista Belaso (1553) and reinvented by Blaise de Vigenère
(1586), called “le chiffre indéchiffrable” for 300 years
• Effectively multiple Caesar ciphers
• Key is a word

• Encryption
• Read one letter t from the plaintext and one letter k from the key-word
• t is encrypted according to the Caesar cipher with key k
• for the next plain-letter, use the next letter from the key-word
• When the key word is finished, start the reading of the key from the beginning
• In other words: ci=(pi+ki mod m) mod 26
• Decryption works in reverse
• Example: key is “bcde”; “testing” is encrypted as “ugvxjpj”
• Note that the two ‘t’ are encrypted by different letters: ‘u’ and ‘x’
• The two ‘j’ in the cryptotext come from different plain letters: ‘i’ and ‘j’

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Vigenère Cipher

https://pages.mtu.edu/~shene/NSF-4/Tutorial/VIG/Vig-Base.html

Vigenère Cipher

For example, suppose

the plaintext is MICHIGAN TECHNOLOGICAL UNIVERSITY
and the keyword is HOUGHTON

https://pages.mtu.edu/~shene/NSF-4/Tutorial/VIG/Vig-Base.html

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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
• if not, then need to determine number of alphabets, 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

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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

One-Time Pad
• if a truly random key as long as the message is used, the cipher will be
secure
• 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

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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:
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

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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

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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

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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

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