<BASIC AND HISTORICAL>

The science of secret writing and its

main branches.

Steganography Code (replace

(hidden) words)
Secret Writing Substitution
Cryptography Cipher (replace
(scrambled) letters)
Transposition
2
STEGANOGRAPHY

THE SAME IMAGE VIEWED BY WHITE, BLUE, GREEN AND RED LIGHTS REVEALS DIFFERENT HIDDEN NUMBERS.

Sources: The Code Book / Singh

https://en.wikipedia.org/wiki/Steganography
STEGANOGRAPHY

• In Greek
• Steganos = covered
• Graphein = to write
• Steganography is about hiding messages
• Historically, secret messages were often hidden (or memorized)
• Today, steganography is used primarily to protect digital rights
• “watermarking” copyright notices
• “fingerprinting” a serial ID

4
HISTORY OF STEGANOGRAPHY
(PHYSICALLY HIDING)
• Runners were memorizing messages
• Sometimes killed after delivering the message

• This is Sparta!! (300-film) 5

HISTORY OF STEGANOGRAPHY
(PHYSICALLY HIDING)
• Demaratus tells Athens of Persia’s attack plans
• Writes the secret message directly on the wooden backing of a wax
tablet before applying its beeswax surface.

Wax tablet and a Roman stylus Writing with stylus and folding
wax tablet. painter, Douris, ca
500 BC

6
HISTORY OF STEGANOGRAPHY
(PHYSICALLY HIDING)
• Greek Histaiaeus encouraged Aristagoras of
Miletus to revolt against the Persian King.
• Writes message on the shaved head of the
messenger, and sends him after his hair grew, with the
instruction, "When thou art come to Miletus, bid
Aristagoras shave thy head, and look thereon."

• Chinese silk balls

• Message is written on silk, turned into wax-covered
ball that was swallowed by the messenger

7
HISTORY OF STEGANOGRAPHY (CONT.)
• Invisible Ink
• Certain organic fluids (milk, fruit juice) are transparent when dried but the deposit can be
charred and is then visible
• Romans used to write between the lines
• A mixture of alum and vinegar may be used to write on hardboiled eggs, so that can only
be read once shell is broken
• Pin punctures: Small pin punctures on selected letters are ordinarily not visible unless the
paper is held up in front of a light

8
HISTORY OF STEGANOGRAPHY (CONT.)

• Invisible Ink (today)

• Invisible ink-jet technology, Ink that is too small for human eye
(Univ of Buffalo, 2000)
• Invisible inks that are only visible under UV light

9
HISTORY OF STEGANOGRAPHY (CONT.)

• Microdots
• is text or an image substantially
reduced in size onto a small disc to
prevent detection by unintended
recipients.
• WW2 Germany - documents shrunk
to the size of a dot, and embedded
within innocent letters
• DNA microdot, embedding
synthetically formed DNA sequence
(secret) into a normal DNA strand,
then posting as microdot
• Microdots with barcode-like
information
10
HISTORY OF STEGANOGRAPHY (CONT.)

• Easter eggs
• Programmers embed in software
• See http://www.eeggs.com
• Claims that Beatles embedded secret messages in
their music http://www.bbc.com/culture/story/20141003-the-hidden-messages-in-songs

11
HIDING A MESSAGE WITHIN A TEXT

• An actual message from a German spy during

world war I
“Apparently, neutral’s protest is thoroughly
discounted and ignored. Isman hard hit. Blockade
issue affect pretext for embargo on by products,
ejecting suets and vegetable oils.”

The codebreakers/Khan
12
HIDING A MESSAGE WITHIN A TEXT

• An actual message from a German spy during world war I

• read second letter in each word
“Apparently, neutral’s protest is thoroughly discounted
and ignored. Isman hard hit. Blockade issue affect
pretext for embargo on by products, ejecting suets and
vegetable oils.”

“Pershing Sails from NY June 1” The codebreakers/Khan

Whoever the sender was, his ingenuity was expanded in
vain, since Pershing actually sailed May 28.
13
HIDING A MESSAGE WITHIN A TEXT
(MORE)
• Shift some words by one point/pixel.
• Shifted words (or their first letters) make the sentence
• Use different fonts
• Letter by letter or word by word (Francis Bacon Cipher)
• Lexical steganography uses the redundancy of the
English language
• “I feel well” and “I feel fine” seem the same, but one may
be used to encode “SOS”
• Chaffing and winnowing
• Riddle text with extra parts that the receiver will know how
to remove (e.g., those that don’t “authenticate”)

14
MODERN STEGANOGRAPHY
• Hiding one message within another (“container”)
• Most containers are rich media
• Images, audio, video are very redundant, can be tweaked without affecting
human eye/ear
• US argued that Bin Laden implanted instructions within taped interviews

• Copyright notices embedded in digital art

• Prove ownership
• Serial number embedded to prevent replication
• Seek infringements on the web using spiders
• Digital cameras EXIF tags
• Not secretive, but hidden from the eye
• Embed info such as camera type, date, shutter speed, focal length,..
15
• Similarly, possible to embed messages in invisible parts of html pages
HIDING A MESSAGE IN AN IMAGE
• Example: use 1-2 Least Significant Bits (LSB) in each
pixel
• human eye wont notice the difference
• message can be compressed to reduce number of bits
needed
• only half the bits are likely to change on average
• prefer “containers” with a lot of variation

• Check out Steganos (www.steganos.com), Digimarc

(www.digimarc.com)

16
EXAMPLE (STEGANOS)
Original Picture Embedded Picture (bombe)

With embedded picture JPG version

17
STEGANALYSIS
• Detection: is there a hidden message?
• Develop signatures for known steganographic tools, e.g. in
LSB method, expect local homogeneity
• When content is encrypted, the message should have a
high entropy (“white noise”)
• Promising results: high detection rates
• Decoding: recover hidden message
• No significant work in this area !
• Prevention: destroy or remove a hidden message
• Most steganographies not robust to image alterations
• Short messages (e.g. copyright) can be encoded
redundantly and survive an alternation 18
STEGANOGRAPHY (SUMMARY)

• Steganography is arguably weaker than

cryptography because the information is revealed
once the message is intercepted

• On the other hand, an encrypted message that is

not hidden may attract attention, and in some cases
may itself incriminate the messenger

• In any event, steganography can be used in

conjunction with cryptography
19
CRYPTOGRAPHY

• Cryptography (or cryptology; from Greek κρυπτός, "hidden, secret";

and γράφειν, graphein, "writing", or -λογία, -logia, "study",
respectively) is the practice and study of techniques for secure
communication in the presence of third parties (called adversaries).
• Modern cryptography intersects the disciplines of mathematics,
computer science, and electrical engineering. Applications of
cryptography include ATM cards, computer passwords, and electronic
commerce.

http://en.wikipedia.org/wiki/Cryptography 20
BASIC TERMINOLOGY

• Plaintext - the original message

• Ciphertext - the 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) - the study of principles/ methods
of deciphering ciphertext without knowing key
• Cryptology - the field of both cryptography and cryptanalysis
21
HISTORY OF CRYPTOGRAPHY
I CAME I SAW I CONQUERED

22
 CIPHER CLASSIFICATION

Ciphers

Symmetric
Public Key Unkeyed
Key

PublicKey Signature ID Random OneWay Hash

Random Signature MAC Symmetric

Classical Stream Block

Our focus today 23

Transposition Substitution
CRYPTOGRAPHY

• transposition of letters
• Scytale is first cryptographic device (Lysander of Sparta 500 BC)
• Message written on a leather strip (the inside of a servant's belt), which is
then unwound to scramble the message.
• Unreadable without proper diameter of wooden rod
• The message warned Lysander that Persia was about to go to war against
him. He immediately set sail and defeated the Persians.

• substitution
• Hebrew ATBASH (‫ )אתבש‬https://en.wikipedia.org/wiki/Atbash
• Kama-Sutra suggests that women learn
th
to encrypt their love messages
by substituting pre-paired letters (4 Century AD)
• Cipher – replace letters 24
• Code – replace words
POLYBIUS SQUARE

• The Greeks also invented a

code which changed letters
into numbers. A is written as
11, B is 12, and so on. So WAR
would read 52 11 42. A form
of this code was still being
used two thousand years
later during the First World
War. Modern variation:
https://en.wikipedia.org/wiki/Bifid_cipher
25
 CAESAR CIPHER

• Simplest and earliest known use of a substitution cipher

• Used by Julius Caesar
• Involves replacing each letter of the alphabet with the letter standing three places
further down the alphabet
• Alphabet is wrapped around so that the letter following Z is A
• Plain: ABCDEFGHIJKLMNOPQRSTUVWXYZ
• Cipher: XYZABCDEFGHIJKLMNOPQRSTUVW

plain: meet me after the toga party

cipher: PHHW PH DIWHU WKH WRJD SDUWB
26
CAESAR CIPHER ALGORITHM

• 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

• Algorithm can be expressed as:

c = E(3, p) = (p + 3) mod (26)

• A shift may be of any amount, so that the general Caesar

algorithm is:
C = E(k , p ) = (p + k ) mod 26
• Where k takes on a value in the range 1 to 25; the
decryption algorithm is simply:
p = D(k , C ) = (C - k ) mod 26 27
 Brute-Force
Cryptanalysis
of
Caesar Cipher

28
MONOALPHABETIC CIPHERS

• Jefferson wheel implementation

https://en.wikipedia.org/wiki/Jefferson_disk
• Set the message across the wheels
• Select another line (in random) as cipher

• Substitution based on key phrase

• Substitution key consists of phrase’s letters
(uniquely) followed by rest of the
alphabet in order
• Phrase: THIS IS ALICE AND BOB’S KEY
• Key: THISALCENDBOKY-FGJMPQRUVWXZ
• 26!=403291461126605635584000000
(4.03291×1026) monoalphabetic
substitution ciphers
29
 BREAKING MONOALPHABETIC CIPHERS
• Relative Frequency of Letters in English Text (or native language)
• https://en.wikipedia.org/wiki/Frequency_analysis

• The Arabs broke monoalphabetic substitution using frequency analysis

• Thus, letters ciphering e, t, and a are easily discovered 30

• Subsequently can look for the rest of the letters and letter pairs
 BREAKING MONOALPHABETIC CIPHERS

• According to the unicity distance of English, 27.6 letters

of ciphertext are required to crack a mixed alphabet
simple substitution.
• In practice, typically about 50 letters are needed,
although some messages can be broken with fewer if
unusual patterns are found.
• https://en.wikipedia.org/wiki/Unicity_distance
31
CÆSAR’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
• So make it longer
• Multiple letters in key
• Idea is to smooth the statistical frequencies to make cryptanalysis
harder
• Use alternate symbols for alphabet like
https://en.wikipedia.org/wiki/Pigpen_cipher 32
HOMOPHONIC SUBSTITUTION
• Homophonic substitution cipher can be used to foil
frequency analysis
• In these ciphers, plaintext letters map to more than
one ciphertext symbol.

33
HOMOPHONIC SUBSTITUTION
• Usually, the highest-frequency plaintext symbols are given more
equivalents than lower frequency letters. In this way, the
frequency distribution is flattened, making analysis more difficult.
• Keyed 2-digit substitution
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

T 06 07 08 09 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 00 01 02 03 04 05
H 43 44 45 46 47 48 49 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42
E 71 72 73 74 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70
K 90 91 92 93 94 95 96 97 98 99 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89

• Reverse frequency
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

06 07 08 09 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 00 01 02 03 04 68 05
43 44 45 46 47 48 49 25 26 29 30 31 32 33 35 36 37 38 40 87
71 73 74 50 53 54 57 59 60 63 64 65 66
90 93 94 97 98 76 78 79 82 83 84
72 51 56 58 61 34 39 86 42
91 95 81 77 80 62 67 88 70
92 52 85 89
75 96 41 34
27 69
55
99
28
 POLYALPHABETIC CIPHERS
• Polyalphabetic substitution cipher
• Improves on the simple monoalphabetic technique by using different
monoalphabetic substitutions as one proceeds through the plaintext
message

All these techniques have the following

features in common:
• A set of related monoalphabetic
substitution rules is used
• A key determines which particular rule is
chosen for a given transformation
35
VIGENERE POLYALPHABETIC CIPHER
• Vigenere’s polyalphabetic cipher (19th century) generalizes
Caesar’s shift cipher
• Use keyword to select encrypting rows Vigenere Tableau
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

A 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

 The Vigenere cipher is B

C
B
C
C
D
D
E
E
F
F
G
G
H
H
I
I
J
J
K
K
L
L
M
M
N
N
O
O
P
P
Q
Q
R
R
S
S
T
T
U
U
V
V
W
W
X
X
Y
Y
Z
Z
A
A
B
D 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

not amenable to simple E

F
G
E
F
G
F
G
H
G
H
I
H
I
J
I
J
K
J
K
L
K
L
M
L
M
N
M
N
O
N
O
P
O
P
Q
P
Q
R
Q
R
S
R
S
T
S
T
U
T
U
V
U
V
W
V
W
X
W
X
Y
X
Y
Z
Y
Z
A
Z
A
B
A
B
C
B
C
D
C
D
E
D
E
F

frequency analysis H
I
H
I
I
J
J
K
K
L
L
M
M
N
N
O
O
P
P
Q
Q
R
R
S
S
T
T
U
U
V
V
W
W
X
X
Y
Y
Z
Z
A
A
B
B
C
C
D
D
E
E
F
F
G
G
H
J J K L M N O P Q R S T U V W X Y Z A B C D E F G H I
K K L M N O P Q R S T U V W X Y Z A B C D E F G H I J
L L M N O P Q R S T U V W X Y Z A B C D E F G H I J K
M M N O P Q R S T U V W X Y Z A B C D E F G H I J K L

 Actually invented earlier N

O
N
O
O
P
P
Q
Q
R
R
S
S
T
T
U
U
V
V
W
W
X
X
Y
Y
Z
Z
A
A
B
B
C
C
D
D
E
E
F
F
G
G
H
H
I
I
J
J
K
K
L
L
M
M
N
P P Q R S T U V W X Y Z A B C D E F G H I J K L M N O

(Giovan Battista Bellaso Q

R
Q
R
R
S
S
T
T
U
U
V
V
W
W
X
X
Y
Y
Z
Z
A
A
B
B
C
C
D
D
E
E
F
F
G
G
H
H
I
I
J
J
K
K
L
L
M
M
N
N
O
O
P
P
S
S S T U V W X Y Z A B C D E F G H I J K L M N O P Q R
16th century) T
U
T
U
U
V
V
W
W
X
X
Y
Y
Z
Z
A
A
B
B
C
C
D
D
E
E
F
F
G
G
H
H
I
I
J
J
K
K
L
L
M
M
N
N
O
O
P
P
Q
Q
R
R
S
S
T
V V W X Y Z A B C D E F G H I J K L M N O P Q R S T U

 Called “le chiffre indéchiffrable” W

X
W
X
X
Y
Y
Z
Z
A
A
B
B
C
C
D
D
E
E
F
F
G
G
H
H
I
I
J
J
K
K
L
L
M
M
N
N
O
O
P
P
Q
Q
36
R
R
S
S
T
T
U
U
V
V
W
Y Y Z A B C D E F G H I J K L M N O P Q R S T U V W X
(The Unbreakable Cipher) Z Z 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
VIGENÈRE CIPHER
• Best known and one of the simplest polyalphabetic
substitution ciphers
• In this scheme the set of related monoalphabetic
substitution rules consists of the 26 Caesar ciphers with
shifts of 0 through 25
• Each cipher is denoted by a key letter which is the
ciphertext letter that substitutes for the plaintext letter a
• Used as the standard field system by the British Army in
World War I and the U.S. Army and other Allied forces
37

during World War II

 EXAMPLE OF VIGENÈRE CIPHER

• To encrypt a message, a key is needed that is as

long as the message
• Usually, the key is a repeating keyword
• For example, if the keyword is deceptive, the
message “we are discovered save yourself” is
encrypted as:
key: deceptivedeceptivedeceptive
plaintext: wearediscoveredsaveyourself 38

ciphertext: ZICVTWQNGRZGVTWAVZHCQYGLMGJ
 (STRONGER) VIGENÈRE AUTOKEY SYSTEM

• A keyword is concatenated with the plaintext itself to provide a running key

• Example:
key: deceptivewearediscoveredsav
plaintext: wearediscoveredsaveyourself
ciphertext: ZICVTWQNGKZEIIGASXSTSLVVWLA
• Since the key is as long as the message, the “Friedman and Kasiski”
tests no longer work, as the key is not repeated.
• 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 39
PLAYFAIR CIPHER
• Best-known multiple-letter encryption cipher
• Treats digrams in the plaintext as single units and translates
these units into ciphertext digrams
• Based on the use of a 5 x 5 matrix of letters constructed
using a keyword
• Invented by British scientist Sir Charles Wheatstone in 1854
• Used as the standard field system by the British Army in
World War I and the U.S. Army and other Allied forces
during World War II 40
PLAYFAIR KEY MATRIX
• Fill in letters of keyword (minus duplicates) from left to right
and from top to bottom, then fill in the remainder of the
matrix with the remaining letters in alphabetic order
• 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 41
 PLAYFAIR CIPHER
Plaintext is encrypted two letters at a time, according to the following rules:

1. Repeating plaintext letters that are in the same pair are separated with a filler letter, such as x, so
that balloon would be treated as ba lx lo on.

2. Two plaintext letters that fall in the same row of the matrix are each replaced by the letter to the
right, with the first element of the row circularly following the last. For example, ar is encrypted as RM.

3. Two plaintext letters that fall in the same column are each replaced by the letter beneath, with the
top element of the column circularly following the last. For example, mu is encrypted as CM.

4. Otherwise, each plaintext letter in a pair is replaced by the letter that lies in its own row and the
column occupied by the other plaintext letter. Thus, hs becomes BP and ea becomes IM (or JM, as
the encipherer wishes).

Assume one wants to encrypt the digram OR. There are five general cases:
1) 2) 3) 4) 5)
* * * * * **O** Z**O* ***** *****
* OY RZ **B ** *** * * ***** **R**
* * * * * ** *** *** * * *ORC* **O**
* * * * * **R ** R**X * ***** ** I**
* * * * * **Y ** *** * * ***** *****
Hence, OR → YZ Hence, OR → BY Hence, OR → ZX Hence, OR → RC Hence, OR → IO
42

https://en.wikipedia.org/wiki/Playfair_cipher
43
TRANSPOSITION CIPHER

• Rearrange letters in plaintext to produce ciphertext

• Example (Rail-Fence Cipher)
• Plaintext is HELLO WORLD
• Rearrange as
HLOOL
ELWRD
• Ciphertext is HLOOL ELWRD

44
TRANSPOSITION CIPHERS
• Railfence with large cycles: TRHCEEIETGSSMAIAEASS

T 5 T R
H 3 H C E E
E 1 I E T G
K 4 S S M A
E 2 I A E S
Y 6 S S

• Railfence (by key): IETGIAESHCEESSMATRSS

• Columnar
T H E K E Y
5 3 1 4 2 6

• IEEIRSHSMESCSTATGSEA T H I S I S
A S E C R E
T M E S S A 45
G E
HILL CIPHER
• Developed by the mathematician Lester Hill in 1929
• Strength is that it completely hides single-letter
frequencies
• The use of a larger matrix hides more frequency information
• A 3 x 3 Hill cipher hides not only single-letter but also two-letter
frequency information

• Strong against a ciphertext-only attack but easily

broken with a known plaintext attack

• https://en.wikipedia.org/wiki/Hill_cipher
46
HISTORICAL CODING
• Louis XIV’s Great Cipher (Rossignols) used one symbol (3-
digit number) per syllable (held 200 years)
• https://en.wikipedia.org/wiki/Great_Cipher
• Mary Queen of Scots used a combination of cipher and
coded words https://en.wikipedia.org/wiki/Babington_Plot
• Referred to as a nomenclature because many codes were for names
• e.g,

• US Army used Navajo language as code in WWII 47

https://en.wikipedia.org/wiki/Code_talker
ATTACKING THE CIPHER, PRINCIPLES IN
DECRYPTION

•Anagramming
• 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

48
EXAMPLE, DECODING RAIL-FENCE

• 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
49
EXAMPLE

•Arrange so the H and E are adjacent

HE
LL
OW
OR
LD
•Read off across, then down, to get original
plaintext
50
BREAKING VIGENERE CIPHER

• Babbage broke Vigenere’s Cipher (1854, Crimean war)

• Stage 1: Discover key length
• Look for repeated sequences, and measure their distance
• The key length is a factor of these distances
• Stage 2: Identify the key itself
• Compare distributions for each of the key letters with the standard distribution,
to identify the shift

• Babbage could not publish his work

• Similar techniques developed independently by Kasiski (a Prussian
officer); Kerckhoff (French cryptographer)

• Check out an applet that breaks Vigenere:

http://math.ucsd.edu/~crypto/java/EARLYCIPHERS/Vigenere.html
51
DECRYPTING THE VIGENERE CIPHER

•We want to break this cipher:

ADQYS MIUSB OXKKT MIBHK IZOOO
EQOOG IFBAG KAUMF VVTAA CIDTW
MOCIO EQOOG BMBFV ZGGWP CIEKQ
HSNEW VECNE DLAAV RWKXS VNSVP
HCEUT QOIOF MEGJS WTPCH AJMOC
HIUIX
52
ESTABLISH PERIOD

• Kaskski: repetitions in the ciphertext occur when

characters of the key appear over the same
characters in the plaintext
• Example:
key VIGVIGVIGVIGVIGV
plain THEBOYHASTHEBALL
cipher OPKWWECIYOPKWIRG
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)
53
REPETITIONS IN EXAMPLE

Letters Start End Distance Factors

MI 5 15 10 2, 5
OO 22 27 5 5
OEQOOG 24 54 30 2, 3, 5
FV 39 63 24 2, 2, 2, 3
AA 43 87 44 2, 2, 11
MOC 50 122 72 2, 2, 2, 3, 3
QO 56 105 49 7, 7
PC 69 117 48 2, 2, 2, 2, 3
NE 77 83 6 2, 3
SV 94 97 3 3
CH 118 124 6 2, 3

Slide #8-54
ESTIMATE OF PERIOD

• OEQOOG is probably not a coincidence

• It’s too long for that
• Period may be 1, 2, 3, 5, 6, 10, 15, or 30
• Most others (7/10) have 2 in their factors
• Almost as many (6/10) have 3 in their factors
• Begin with period of 2  3 = 6

55
CHECK ON PERIOD

• Index of coincidence is probability that two randomly

chosen letters from ciphertext will be the same
• Tabulated for different periods:
1 0.066 3 0.047 5 0.044
2 0.052 4 0.045 10 0.041
Large 0.038

56
COMPUTE IC

•IC = [n (n – 1)]–1 0≤i≤25 [Fi (Fi – 1)]

• where n is length of ciphertext and Fi the number of
times character i occurs in ciphertext

•Here, IC = 0.043
• Indicates a key of slightly more than 5
• A statistical measure, so it can be in error, but it agrees
57

with the previous estimate (which was 6)

SPLITTING INTO ALPHABETS

alphabet 1: AIKHOIATTOBGEEERNEOSAI
alphabet 2: DUKKEFUAWEMGKWDWSUFWJU
alphabet 3: QSTIQBMAMQBWQVLKVTMTMI
alphabet 4: YBMZOAFCOOFPHEAXPQEPOX
alphabet 5: SOIOOGVICOVCSVASHOGCC
alphabet 6: MXBOGKVDIGZINNVVCIJHH
• ICs (#1, 0.069; #2, 0.078; #3, 0.078; #4, 0.056;
#5, 0.124; #6, 0.043) indicate all alphabets have
period 1, except #4 and #6; assume statistics off

58
FREQUENCY EXAMINATION

ABCDEFGHIJKLMNOPQRSTUVWXYZ
1 31004011301001300112000000
2 10022210013010000010404000
3 12000000201140004013021000
4 21102201000010431000000211
5 10500021200000500030020000
6 01110022311012100000030101
Letter frequencies are (H high, M medium, L low):
HMMMHMMHHMMMMHHMLHHHMLLLLL
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BEGIN DECRYPTION

• First matches characteristics of unshifted alphabet

• Third matches if I shifted to A
• Sixth matches if V shifted to A
• Substitute into ciphertext (bold are substitutions)
ADIYS RIUKB OCKKL MIGHK AZOTO EIOOL
IFTAG PAUEF VATAS CIITW EOCNO EIOOL
BMTFV EGGOP CNEKI HSSEW NECSE
DDAAA RWCXS ANSNP HHEUL QONOF
EEGOS WLPCM AJEOC MIUAX
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LOOK FOR CLUES

• AJE in last line suggests “are”, meaning second alphabet

maps A into S:
ALIYS RICKB OCKSL MIGHS AZOTO
MIOOL INTAG PACEF VATIS CIITE
EOCNO MIOOL BUTFV EGOOP CNESI
HSSEE NECSE LDAAA RECXS ANANP
HHECL QONON EEGOS ELPCM AREOC
MICAX
61
NEXT ALPHABET

• MICAX in last line suggests “mical” (a common ending

for an adjective, like comical), meaning fourth
alphabet maps O into A:
ALIMS RICKP OCKSL AIGHS ANOTO MICOL
INTOG PACET VATIS QIITE ECCNO MICOL
BUTTV EGOOD CNESI VSSEE NSCSE LDOAA
RECLS ANAND HHECL EONON ESGOS ELDCM
ARECC MICAL
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GOT IT!

• QI means that U maps into I, as Q is always followed by U:

ALIME RICKP ACKSL AUGHS ANATO
MICAL INTOS PACET HATIS QUITE
ECONO MICAL BUTTH EGOOD ONESI
VESEE NSOSE LDOMA RECLE ANAND
THECL EANON ESSOS ELDOM ARECO
MICAL
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THE REAL MESSAGE IS

• A LIMERICK PACKS LAUGHS ANATOMICAL INTO SPACE

THAT IS QUITE ECONOMICAL BUT THE GOOD ONES I’VE
SEEN SO SELDOM ARE CLEAN, AND THE CLEAN ONES
SO SELDOM ARE COMICAL

• Feinberg, Leonard. The Secret of Humor. Rodopi, 1978. ISBN 9789062033706. p102
64
UNBREAKABLE ENCRYPTION
• One time pads
• Sender and receiver use a pre-arranged random stream of letters
• Encryption=addition modulo 26 M E S S A G E
• XOR when binary T H I S K E Y
• Every letter in the key used only once
F L A K K K C
• One time pads provide for the only perfectly secure
encryption algorithms
• Why? Look at ciphertext DXQR. Equally likely to correspond to
plaintext DOIT (key AJIY) and to plaintext DONT (key AJDY) and
any other 4 letters
• All the rest are only computationally secure
• Used by Soviet spies, and also for US-USSR hotline.
• https://en.wikipedia.org/wiki/One-time_pad 65
EXAMPLE OF ONE-TIME PAD

66
ONE-TIME PAD FUNDAMENTAL DIFFICULTIES

• Relies on randomness of key. Otherwise you can attack the

cipher by trying to regenerate the key

• Approximations, such as using pseudorandom number

generators to generate keys, are not random
67

• Limited utility: is useful primarily for low-bandwidth channels

SUMMARY OF HISTORICAL CRYPTO

• Encryption Algorithms and Keys

• Substitution : letters (bits), words
• Transposition
• Decryption Algorithms
• Reversed process
• Require knowledge of the algorithm and the key
• Cryptanalysis
• Identify algorithm
• Obtain as many plaintext-ciphertext pairs
• Use systematicity (patterns)
• Use hints (cribs)
68
MODERN CRYPTOGRAPHY
RISE OF THE MACHINES

69

Main source: Network Security Essentials / Stallings

KERCKHOFFS PRINCIPLES: SYSTEM + KEYS
1. The system must be substantially, if not mathematically,
undecipherable;
2. The system must not require secrecy and can be stolen by the
enemy without causing trouble;
3. It must be easy to communicate and remember the keys without
requiring written notes, it must also be easy to change or modify the
keys with different participants;
4. The system ought to be compatible with telegraph communication;
5. The system must be portable, and its use must not require more
than one person;
6. Finally, regarding the circumstances in which such system is
applied, it must be easy to use and must neither require stress of
mind nor the knowledge of a long series of rules.
70
August Kerckhoffs, Journal of Military Science, 1883
 THE GERMAN ENIGMA
• Invented as a commercial machine (Scherbius at end of
WWI), and failed
• Electrical typewriter-like encryption machine
• Each keystroke lights a letter
• Performing substitutions
• Letter-pairs are switched
• Pulse goes through scramblers
• Hits reflector and goes back
• Original Enigma (M3) based on commercial version
• Reconfigurable 6 swapped letter-pairs
• 3 rotating scramblers (263 orientations)
• scramblers can be configured in 6 (3!) ways
• Later, up to 5 scramblers to choose from
• Theoretical key space = a total of 1017 combinations
https://en.wikipedia.org/wiki/Enigma_machine
71
 THE GERMAN ENIGMA

• Before war broke out in 1939 the

German army, navy and air force
were told to encode their messages
using the enigma machine
• The Germans believed that no one
could crack the Enigma code. But
the Allies knew that if they could,
they would be able to find out their
enemy's military secrets.
• At least once a day the Germans
changed the order of the rotors,
their starting positions and the
plugboard connections. To decipher
a message sent using Enigma, you
had to work out exactly how all of
these had been set

• Try out an enigma emulator 72

• http://users.telenet.be/d.rijmenants/en/en
igmasim.htm
POLES CRACK THE ENIGMA

• Polish obtained an Enigma from a German spy (1933)

• Hans-Thilo Schmidt sold to French intelligence
• Obtained information on its usage
• daily code book indicated rotors and orientation
• a different orientation key for each message
• Rejewski focused on the repetitions
• Message key encrypted twice in the message header
• Formalized relationships between 1st-4th ,2nd-5th, and 3rd-6th letters
• ABCDEFGHIJKLMNOPQRSTUVWXYZ
• FQHPLWOGBMVRXUYCZITNJEASDK
• Built chains
• (AFW), (BQZKVELRI), (CHGOYDP), (JMXSTNU)
• Chains depend only on scrambler orientation, not on pairs swaps
• Thus need to consider only 3! x 263 = 105456 configurations
• Built a catalog of characteristic chains for all configurations

73
POLES CRACK THE ENIGMA
• Rejewski’s algorithm to discover the day key
• First, use catalog to identify the scrambler setting and orientation
• Then, run the ciphertext through an Enigma and look at the text to
identify swapped letter pairs
https://en.wikipedia.org/wiki/Cryptanalysis_of_the_Enigma
• Bombe machines were constructed to mechanize the search
• A one-ton machine that essentially stringed together 6 Enigmas
(one for each ordering of the scramblers)

74
BRITISH CRACK IMPROVED ENIGMA

• In 1939, Germans increased Enigma security

• Navy admiral added 2 extra scramblers to choose
from – 10x arrangements (5 choose 3, times the 3!
orderings)
• Hitler used a more complex version – Lorenz Cipher
• increased to 10 letter pair swaps

• British (Bletchley Park) continued where the Polish

left
• Recruited best Mathematicians (Turing) and large staff
(7000)
• Did not make much progress until received Bombes
from Polish

• Used human weaknesses. Provided hints and cribs

• Trivial message keys (key sequences, names initials)
• Artificial restrictions on scramblers selection/orientation
• Standard messages (weather) sent with 4th scrambler
neutralized 75
• Some German codebooks were captured
BRITISH CRACK IMPROVED ENIGMA

• Turing built swap-independent chains (a la Rejewski)

• First British Bombe (Victory) delivered in 1940
• Search still required significant human help
• In 1942, Germans add 4th active scrambler (M4)
• Bletchley Park could not decipher M4’s messages for 10 months
• Could only break it when info was captured in u-boats
• Captured machines, rotors, weather manuals, providing cribs
• Later in the war, US Navy also constructed even faster and
more sophisticated bombes
• Japanese used PURPLE, a machine modeled after Enigma
• Pearl Harbor Attack was broken hours before the attack

• The British ULTRA – broken German, Italian and Japanese

76
communications were crucial to winning the war
COMPUTER AND CODE
BREAKING
• Colossus was built
for the code-
breakers at
Bletchley Park by
post office
engineers in 1943.
• One of the earliest
digital computers.

77
 Computer and Code Breaking
• The computer was as big
as a room 5 metres long,
3 metres deep and 2.5
metres high - and was
made mainly from parts
used for post office
telephone and telegraph
systems.

78
SIGABA
• It was suited for fixed
station secure
communications, and used
by U.S. for high-level
communications, was the
only machine system used
by any participant to
remain completely
unbroken by an enemy
during World War II.

79
B-21 MACHINE BY BORIS
HAGELIN
• Patterned on the
Enigma and produced
for the Swedish
General staff, Boris
Hagelin of Sweden
developed the B-21
machine in 1925. It also
had the capability to be
connected to an electric
typewriter.
80
BC-38 BY CRYPTO AG ZUG

• Boris Hagelin of
Sweden developed a
long line of cipher
systems, beginning
with the B-21, B-211,
C-35, C-36, C-38
(which later became
America's M-209).

81
BID 590 (NOREEN)
• The BID 590 was a
British built crypto
machine and was used
by Canada's foreign
service communicators
at various diplomatic
missions to
communicate with
various government
departments.
82
H-4605 (CRYPTO AG)
• The Crypto AG H4605
was designed as an off-
line, keyboard operated
cipher machine with twin
printing (of cipher and
plain text) system with
automatic 5-letter
grouping. It's a solid piece
of equipment, almost
'battleship grade’.

83
JAPANESE "ENIGMA"
ROTOR CIPHER MACHINE

Produced by Germans for Japanese, code name “green” by Americans

84
 Japanese Purple machine
• Electromechanical stepping switch machine modeled
after enigma https://en.wikipedia.org/wiki/Type_B_Cipher_Machine
• Used telephone stepping switches instead of rotots
• Purple was broken with the help of MAGIC
• Pear Harbor attack preparations encoded in Purple,
decoded hours before attack

85
KY-28 (NESTOR)

• The KY-28 was an

analog, voice
encryption device
based on transistor
circuitry and was the
shipboard/airborne
member of the
NESTOR family of
equipment.

86
RACAL-MILGO 64-1027C
DATACRYPTOR
• The Racal-Milgo 64-
1027C Datacryptor was
used to send and
receive secure data via
computer. This is the
commercial version of
the KG-84, and has
ability to be loaded via
the KYK-13 Fill device.

87
THE “CLOCK CRYPTOGRAPH”

• It is basically a nicely
implemented
Wheatstone cipher
disk. It was in active
use in the Danish
armed forces from
1934 (or a little
earlier) until around
1948.

88
COMPUTER AND CODE
BREAKING
• This Cray XMP was donated
to the museum by Cray
Research, Inc. It denotes
the newest era of
partnership between NSA
and the American computer
industry in the employment
of computers for
cryptologic processes.
89
NEVER-ENDING CIPHERS

• Many more historical machines than time permits, but visit

http://users.telenet.be/d.rijmenants/en/timeline.htm
• And many other classical ciphers, continue your studies at:
http://practicalcryptography.com/ciphers/classical-era/
• http://williamstallings.com/Extras/Security-Notes/lectures/classical.html
• For a good series of video, look at the Khan academy course:
• https://www.khanacademy.org/computing/computer-science/cryptography
• Ready to jump to the deep end of the pool, take the free “mooc” course:
• https://www.coursera.org/learn/crypto 90
 FURTHER READING
The Codebreakers: The Comprehensive History of
Secret Communication from Ancient Times to the
Internet / Kahn

The Code Book: The Science of Secrecy from

Ancient Egypt to Quantum Cryptography/Singh

Introduction to Modern Cryptography / Katz & Lindell

Foundations of Cryptography / Goldreich.

Graduate-level text.

91