Cryptography and

Network Security
Chapter 2
 Symmetric Encryption
 or conventional / private-key / single-key
 sender and recipient share a common key
 all classical encryption algorithms are
private-key was the only type prior to
invention of public key in 1970’s
 and by far the most widely used (still)
 is significantly faster than public-key crypto
 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 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
Model of Symmetric Cryptosystem

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 Cryptography
 can characterize cryptographic system by:
 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
 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 and 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
 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 25 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"
Three important characteristics of this problem
enabled us to use a brute force cryptanalysis:
1. The encryption and decryption algorithms are
known.
2. There are only 25 keys to try.
3. The language of the plaintext is known and
easily recognizable.

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 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 26 characters…
 now have a total of 26! = 4 x 1026keys
 with so many keys, might think is secure
 but would be !!!WRONG!!!
 problem is language characteristics
 Language Redundancy and
Cryptanalysis
 human languages are redundant
 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
 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
 mo -> ON; ve -> UF; fo -> PH, etc.
 Ciphertext = ON UF PH NZ RM BZ
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
 use each key letter as a Caesar cipher key
 encrypt the corresponding plaintext letter
 eg using keyword deceptive
key:deceptivedeceptivedeceptive
plaintext: wearediscoveredsaveyourself
ciphertext:ZICVTWQNGRZGVTWAVZHCQYGLMGJ
 Aids
 simple aids can assist with en/decryption
 a Saint-Cyr Slide is a simple manual aid
 a slide with repeated alphabet
 line up plaintext 'A' with key letter, eg 'C'
 then read off any mapping for key letter
 can bend round into a cipher disk
 or expand into a Vigenère Tableau
 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
 ifnot, 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
 Homework 1
 Due next class
 Question 1:
What is the best “flattening” effect you can
achieve by carefully selecting two
monoalphabetic substitutions? Explain
and give an example. What about three
monoalphabetic substitutions?
 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
 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
 Homophone Cipher
 rather than combine multiple monoalphabetic
ciphers, can assign multiple ciphertext
characters to same plaintext character
 assign number of homophones according to
frequency of plaintext character
 Gauss believed he made unbreakable cipher
using homophones
 but still have digram/trigram frequency
characteristics to attack
 e.g., have 58 ciphertext characters, with each
plaintext character assigned to ceil(freq/2)
ciphertext characters – so e has 7 homophones,
t has 5, a has 4, j has 1, q has 1, etc.
 Vernam Cipher
 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
 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:
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
 writeletters 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: 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: 4931285607
Plaintext: attackpost poneduntil twoamxyzab

Ciphertext: CTATTSKPAO DLEONIDUPT MBAWOAXYTZ

 Homework 1
 Due next class
 Question 2:
Mathematically specify an arbitrary block
transposition cipher with block length B
and permutation :[0..B-1] → [0..B-1] for
plaintext P=p0p1p2p3…pN-1, where N is a
multiple of B.
 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
 Homework 1
 Due next class
 Question 3: (be mathematical)
a. What is the result of the product of two
rotational substitutions?
b. What is the result of the product of two
affine substitutions?
c. What is the result of the product of two
block transpositions?
 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
 Homework 1
 Due next class
 Question 4:
Give a mathematical description of a two-
rotor cipher.
 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