Itis 3200 introduction to information security and privacy
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ITIS 3200: Introduction to Information Security and Privacy. Dr. Weichao Wang. Chapter 8: Basic Cryptography. Classical Cryptography Public Key Cryptography Cryptographic Checksums. Overview. Classical Cryptography (symmetric encryption) Caesar cipher Vigenère cipher DES

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Itis 3200 introduction to information security and privacy

ITIS 3200:Introduction to Information Security and Privacy

Dr. Weichao Wang

Chapter 8 basic cryptography

Chapter 8: Basic Cryptography

  • Classical Cryptography

  • Public Key Cryptography

  • Cryptographic Checksums



  • Classical Cryptography (symmetric encryption)

    • Caesar cipher

    • Vigenère cipher

    • DES

  • Public Key Cryptography (asymmetric encryption)

    • RSA

  • Cryptographic Checksums



  • Quintuple (E, D, M, K, C)

    • M set of plaintexts

    • K set of keys

    • C set of ciphertexts

    • E set of encryption functions e: M KC

    • D set of decryption functions d: C KM

    • Usually, the cipher text is longer than or has the same length as the plaintext, why?



  • Example: Caesar cipher (a circular shift mapping)

    • M = { sequences of letters }

    • K = { i | i is an integer and 0 ≤ i ≤ 25 }

    • E = { Ek | kK and for all letters m,

      Ek(m) = (m + k) mod 26 }

    • D = { Dk | kK and for all letters c,

      Dk(c) = (26 + c – k) mod 26 }

    • From the space point of view, C = M



  • Opponent whose goal is to break cryptosystem is the adversary

    • Assume adversary knows algorithm used, but not key

    • They are after the key and/or data contents

  • Three types of attacks:

    • ciphertext only: adversary has only ciphertext; goal is to find plaintext, possibly key

    • known plaintext: adversary has ciphertext, corresponding plaintext; goal is to find key

    • chosen plaintext: adversary may supply plaintexts and obtain corresponding ciphertext; goal is to find key

    • It is not difficult to know both ciphertext and plaintext

Basis for attacks

Basis for Attacks

  • Mathematical attacks

    • Based on analysis of underlying mathematics

    • For example: the safety of RSA is based on the difficulty to factor the product of two large prime numbers. If it is broken, the RSA will become unsafe.

  • Statistical attacks

    • Make assumptions about the distribution of letters, pairs of letters (digrams), triplets of letters (trigrams), etc.

      • Called models of the language

    • Examine ciphertext, correlate properties with the assumptions.

Classical cryptography symmetric

Classical Cryptography (symmetric)

  • Sender, receiver share common key

    • Keys may be the same, or trivial to derive one from the other

    • Sometimes called symmetric cryptography

    • How to distribute keys: following chapters

  • Two basic types

    • Transposition ciphers (shuffle the order)

    • Substitution ciphers (replacement)

    • Combinations are called product ciphers

Transposition cipher

Transposition Cipher

  • Rearrange letters in plaintext to produce ciphertext

  • Example (Rail-Fence Cipher)

    • Plaintext is HELLO WORLD

    • Rearrange as



    • Ciphertext is HLOOL ELWRD

Attacking the cipher

Attacking the Cipher

  • Anagramming

    • The frequency of the characters will not change

    • The key is a permutation function

    • If 1-gram frequencies match English frequencies, but other n-gram frequencies do not, probably transposition

    • Rearrange letters to form n-grams with highest frequencies



  • Ciphertext: HLOOLELWRD

  • Frequencies of 2-grams beginning with H

    • HE 0.0305

    • HO 0.0043

    • HL, HW, HR, HD < 0.0010

  • Frequencies of 2-grams ending in H

    • WH 0.0026

    • EH, LH, OH, RH, DH ≤ 0.0002

  • Implies E follows H



  • Arrange so the H and E are adjacent






  • Read off across, then down, to get original plaintext

  • May need to try different combinations or n-grams

Itis 3200 introduction to information security and privacy

  • Under many conditions, transposition cipher alone is not enough:

    • Example: is it “cat” or “act”

    • Example: I will come, she will not.

Substitution ciphers

Substitution Ciphers

  • Change characters in plaintext to produce ciphertext

    • The replacement rule can be fixed or keep changing

  • Example (Caesar cipher)

    • Plaintext is HELLO WORLD

    • Change each letter to the third letter after it in the alphabet (A goes to D, ---, X goes to A, Y to B, Z to C)

      • Key is 3, usually written as letter ‘D’

    • Ciphertext is KHOOR ZRUOG

Attacking the cipher1

Attacking the Cipher

  • Exhaustive search

    • If the key space is small enough, try all possible keys until you find the right one

    • Caesar cipher has 26 possible keys

    • On average, you only need to try half of them

  • Statistical analysis

    • The ciphertext has a character frequency

    • Compare (and try to align it) to 1-gram model of English

Statistical attack

Statistical Attack

  • Compute frequency of each letter in ciphertext:



  • Apply 1-gram model of English

    • Frequency of characters (1-grams) in English is on next slide

Character frequencies

Character Frequencies

Itis 3200 introduction to information security and privacy

Frequency chart of English

Frequency chart of ciphertext

Statistical analysis

Statistical Analysis

  • Try to align the two charts

  • f(c): frequency of character c in ciphertext

  • (i): correlation of frequency of letters in ciphertext with corresponding letters in English, assuming key is i

    • (i) = 0 ≤ c ≤ 25f(c)p(c – i)

    • (i) = 0.1p(6 – i) + 0.1p(7 – i) + 0.1p(10 – i) + 0.3p(14 – i) + 0.2p(17 – i) + 0.1p(20 – i) + 0.1p(25 – i)

      • p(x) is frequency of character x in English

    • This correlation value should be a maximum when the two charts are aligned

Correlation i for 0 i 25

Correlation: (i) for 0 ≤ i ≤ 25

The result

The Result

  • Most probable keys, based on :

    • i = 6, (i) = 0.0660

      • plaintext EBIIL TLOLA

    • i = 10, (i) = 0.0635

      • plaintext AXEEH PHKEW

    • i = 3, (i) = 0.0575

      • plaintext HELLO WORLD

    • i = 14, (i) = 0.0535

      • plaintext WTAAD LDGAS

  • Only English phrase is for i = 3

    • That’s the key (3 or ‘D’)

  • The algorithm will become more complicated if the encryption is not a circular shift

  • We are only reducing the searching space by guided guess

Caesar s problem

Caesar’s Problem

  • Key is too short

    • Can be found by exhaustive search

    • Statistical frequencies not concealed well

      • They look too much like regular English letters

        • The most frequently seen character could be “E”

  • So make it longer

    • Multiple letters in key

    • Idea is to smooth the statistical frequencies to make cryptanalysis harder

      • What if in the cipher text, every character has the same frequency?

      • All correlation will have the same value

Itis 3200 introduction to information security and privacy

  • What we can get from this:

    • If the key contains only 1 character, we have 26 choices

    • If the key contains m characters, we need to try 26 ^ m combinations. m=5, 12 million choices.

Vigen re cipher

Vigenère Cipher

  • Like Caesar cipher, but use a longer key

  • Example

    • Message THE BOY HAS THE BALL

    • Key VIG (right shift 21, 8, 6 times, then start again)

    • Encipher using Caesar cipher for each letter:



      cipher OPK WWE CIY OPK WIRG

Itis 3200 introduction to information security and privacy

  • Now we have:

    • Three groups of characters encrypted by V, I, and G respectively

    • Each group is a Caesar cipher (fixed shift offset)

    • Approach:

      • Figure out the length of the key

      • Decipher each group as a Caesar’s cipher

    • Hint: when the same plaintext is encrypted by the same segment of key, we have the same cipher

      • Can be used to derive the period

Attacking the cipher2

Attacking the Cipher

  • Approach

    • Establish period; call it n

    • Break message into n parts, each part being enciphered using the same key letter

      • So each part is like a Caesar cipher

    • Solve each part

      • You can leverage one part from another because English has its special rule

Establish period

Establish Period

  • Kasiski: repetitions in the ciphertext occur when characters of the key appear over the same characters in the plaintext

  • Example:




    Note the key and plaintext line up over the repetitions (underlined). As distance between repetitions is 9, the period is a factor of 9 (that is, 1, 3, or 9)

Itis 3200 introduction to information security and privacy

  • We guess the period is 3, so we divide the cipher text into three groups

    • Each group is a Caesar cipher

    • Using previous approaches to solve them

One time pad

One-Time Pad

  • A Vigenère cipher with a random key at least as long as the message

    • Provably unbreakable

    • Why? Every character in the key is random. It has the same chance to be “a”, “b”, ---, “z”

    • Look at ciphertext DXQR. Equally likely to correspond to plaintext DOIT (key AJIY) and to plaintext DONT (key AJDY) and any other 4-letter words

    • Warning: keys must be random, or you can attack the cipher by trying to regenerate the key

Overview of the des

Overview of the DES

  • A block cipher:

    • encrypts blocks of 64 bits using a 64 bit key

    • outputs 64 bits of ciphertext

  • A product cipher

    • basic unit is the bit

    • performs both substitution and transposition (permutation) on the bits

  • Cipher consists of 16 rounds (iterations), each with a 48-bit round key generated from the 64-bit key

Generation of round keys

Generation of Round Keys

  • Round keys are 48 bits each



The f function

The f Function

Itis 3200 introduction to information security and privacy

  • S-Box

    • There are eight S-Box, each maps 6-bit input to 4-bit output

    • Each S-Box is a look-up table

    • This is the only non-linear step in DES and contributes the most to its safety

  • P-Box

    • A permutation



  • Considered too weak

    • Diffie, Hellman said “in a few years technology would allow DES to be broken in days”

      • DES Challenge organized by RSA

      • In 1997, solved in 96 days; 41 days in early 1998; 56 hours in late 1998; 22 hours in Jan 1999


    • Design decisions not public

      • S-boxes may have backdoors

Undesirable properties

Undesirable Properties

  • 4 weak keys

    • They are their own inverses

  • 12 semi-weak keys

    • Each has another semi-weak key as inverse

  • Complementation property

    • DESk(m) = c DESk(m) = c

  • S-boxes exhibit irregular properties

    • Distribution of odd, even numbers non-random

    • Outputs of fourth box depends on input to third box

Itis 3200 introduction to information security and privacy

  • Number of rounds

    • After 5 rounds, every cipher bit is impacted by every plaintext bit and key bit

    • After 8 rounds, cipher text is already a random function

    • When the number of rounds is 16 or more, brute force attack will be the most efficient attack for known plaintext attack

    • So NSA knows a lot when it fixes the DES

Differential cryptanalysis

Differential Cryptanalysis

  • A chosen ciphertext attack

    • Requires 247 (plaintext, ciphertext) pairs

  • Revealed several properties

    • Small changes in S-boxes reduce the number of (plaintext, ciphertext) pairs needed

    • Making every bit of the round keys independent does not impede attack

  • Linear cryptanalysis improves result

    • Requires 243 (plaintext, ciphertext) pairs

Des modes

DES Modes

  • Electronic Code Book Mode (ECB)

    • Encipher each block independently

  • Cipher Block Chaining Mode (CBC)

    • Xor each plaintext block with previous ciphertext block

    • Requires an initialization vector for the first one

    • The initialization vector can be made public

  • Encrypt-Decrypt-Encrypt Mode (2 keys: k, k)

  • Encrypt-Encrypt-Encrypt Mode (3 keys: k, k, k)

Cbc mode encryption

init. vector









CBC Mode Encryption

Cbc mode decryption

CBC Mode Decryption

init. vector







Self healing property

Self-Healing Property

  • What will happen if a bit gets lost during transmission?

    • All blocks will not be aligned

  • When one bit in a block flipped, only the next two blocks will be impacted.

    • Plaintext “heals” after 2 blocks

Current status of des

Current Status of DES

  • Design for computer system, associated software that could break any DES-enciphered message in a few days published in 1998

  • Several challenges to break DES messages solved using distributed computing

  • NIST selected Rijndael as Advanced Encryption Standard, successor to DES

    • Designed to withstand attacks that were successful on DES

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