CYS505 Network Security

Prepared By: Dr. Ihab ELAFF

Classical Encryption Techniques
 2.1 Symmetric Cipher Model
◦ Cryptography
◦ Cryptanalysis
 2.2 Substitution Techniques
◦ Caesar Cipher
◦ Monoalphabetic Ciphers
◦ Playfair Cipher
◦ Polyalphabetic Ciphers
◦ Vigenère Cipher
◦ One-Time Pad
 2.3 Transposition Techniques
 2.4 Rotor Machines
 2.5 Steganography
 plaintext - the original message
 ciphertext - the coded message
 cipher - algorithm for transforming plaintext/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) - the study of principles/
methods of deciphering ciphertext without knowing key
 cryptology - the field of both cryptography and
cryptanalysis
State-of-the-art: two kinds of most popular
encryption algorithms
 Symmetric ciphers
◦ Sender and receiver share a common key
 Public key ciphers
◦ Sender and receiver have asymmetric information of
the key(s)
 Symmetric Encryption or conventional /
private-key Encryption / single-key
Encryption
 was only type prior to invention of public-key
in 1970’s
 remains very widely used
 sender and recipient share a common key
◦ Both parties have full information of the key
 all classical encryption algorithms are
common key (private-key)
◦ Characteristic of conventional algorithms
 two requirements for secure use of symmetric
encryption:
◦ a strong encryption algorithm (keeping key secret is
sufficient for security)
◦ a secret key known only to sender / receiver
Y = EK(X)
X = DK(Y)
 assume encryption algorithm is known
 implies a secure channel to distribute key
 can characterize by:
◦ type of encryption operations used
 substitution / transposition / product systems
◦ number of keys used
 single-key or private / two-key or public
◦ way in which plaintext is processed
 Block: process one block of elements a time
 Stream: continuous input, output one element a time
Type of Known to Cryptanalyst
Attack
ciphertext • Encryption algorithm
only • Ciphertext
Known • Encryption algorithm
plaintext • Ciphertext
• One or more plaintext-ciphertext pairs formed with the secret key
Chosen • Encryption algorithm
plaintext • Ciphertext
• Plaintext message chosen by cryptanalyst, together with its
corresponding
• ciphertext generated with the secret key
Chosen • Encryption algorithm
ciphertext • Ciphertext
• Purported ciphertext chosen by cryptanalyst, together with its
• corresponding decrypted plaintext generated with the secret key
Chosen • Encryption algorithm
text • Ciphertext
• Plaintext message chosen by cryptanalyst, with its corresponding
• ciphertext generated with the secret key
• Purported ciphertext chosen by cryptanalyst, together with its
• corresponding decrypted plaintext generated with the secret key
 always possible to simply try every key
 most basic attack, proportional to key size
 assume either know / recognise plaintext
 Caesar Cipher
 Monoalphabetic Ciphers
 Playfair Cipher
 Hill Cipher
 Polyalphabetic Ciphers
 One-Time Pad
 Examine a sampling of what might be called
classical encryption techniques.
 Illustrate the basic approaches to symmetric
encryption and the types of cryptanalytic
attacks that must be anticipated.
 The two basic building blocks of all
encryption techniques: substitution and
transposition.
 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
 earliest known substitution cipher
 by Julius Caesar
 first attested use in military affairs
 replaces each letter by a letter three places
down the alphabet
 example:
meet me after the toga party
PHHW PH DIWHU WKH WRJD SDUWB
 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
0 1 2 3 4 5 6 7 8 9 10 11 12
n o p q r s t u v w x y Z
13 14 15 16 17 18 19 20 21 22 23 24 25
 then have Caesar cipher as:
C = E(p) = (p + k) mod (26)
p = D(C) = (C – k) mod (26)
◦ modulo arithmetic: 1 = 27 mod 26, 3 = 29 mod 26
 only have 26 possible keys
◦ Could shift K = 0, 1, 2, …, 25 slots
 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
 Test:break ciphertext
GCUA VQ DTGCM
 rather than just shifting the alphabet
 could shuffle 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
 now have a total of 26! = 4 x 10^26 keys
 with so many keys, might think is secure
◦ The simplicity and strength of the monoalphabetic
substitution cipher dominated for the first
millenium AD.
 but would be !!!WRONG!!!
◦ First broken by Arabic scientists in 9th century
 letters are not equally commonly used
 in English e is by far the most common
letter
 then T,R,N,I,O,A,S
 other letters are fairly rare
 cf. Z,J,K,Q,X
 have tables of single, double & triple letter
frequencies
 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
 for monoalphabetic must identify each
letter
◦ tables of common double/triple letters help
 given ciphertext:
UZQSOVUOHXMOPVGPOZPEVSGZWSZOPFPESXUDBMETSXAIZ
VUEPHZHMDZSHZOWSFPAPPDTSVPQUZWYMXUZUHSX
EPYEPOPDZSZUFPOMBZWPFUPZHMDJUDTMOHMQ
 count relative letter frequencies
 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
 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
 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
 plaintext encrypted two letters at a time:
1. he plaintext is split into pairs of two letters
(digraphs). If there is an odd number of letters,
a Z is added to the last letter.
2. if a pair is a repeated letter, insert a filler like
'X', eg. "balloon" encrypts as "ba lx lo on"
3. if both letters fall in the same row, replace each
with letter to right (wrapping back to start from
end), eg. “ar" encrypts as "RM"
4. if both letters fall in the same column, replace
each with the letter below it (again wrapping to
top from bottom), eg. “mu" encrypts to "CM"
5. otherwise each letter is replaced by the one in
its row in the column of the other letter of the
pair, eg. “hs" encrypts to "BP", and “ea" to "IM"
or "JM" (as desired)
 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. US &
British military in WW1)
 it can be broken, given a few hundred letters
 since still has much of plaintext structure
 another approach to improving security is
to use multiple cipher alphabets
 called polyalphabetic substitution ciphers
 makes 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
 key: deceptivedeceptivedeceptive
plaintext: wearediscoveredsaveyourself
ciphertext:ZICVTWQNGRZGVTWAVZHCQYGLMGJ
 write the plaintext out
 write the keyword repeated above it
◦ eg using keyword deceptive
◦ d order 4th letter  Add 4-1 = 3
◦ e order 5th letter  Add 5-1 = 4
◦ c order 3rd letter  Add 3-1 = 2
 use each key letter as a Caesar cipher key
 encrypt the corresponding plaintext letter
 simplest polyalphabetic substitution cipher is
the Vigenère Cipher
 effectively multiple caesar ciphers
 key is d-letter 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
 The Modern Vigenère Tableau
 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
 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
◦ No repetition of patterns
 since for any plaintext & any ciphertext
there exists a key mapping one to other
 can only use the key once though
 have problem of safe distribution of key
 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
 write message letters out diagonally over a
number of rows then read off cipher row by
row
 eg. write message “meet me after the toga
party” 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
 a more complex scheme 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: 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
 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
 Multiple-stage substitution algorithms
 before modern ciphers, rotor machines
were most common product cipher
 were 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
 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 graphic image or sound file
 has drawbacks
◦ high overhead to hide relatively few info bits