CRYPTOLOGY

WITH CRYPTOOL V 1.4.30

Practical Introduction to
Cryptography and Cryptanalysis

Scope, Technology, and Future of CrypTool

www.cryptool.org
Prof. Bernhard Esslinger and the CrypTool Team, July 2010
www.cryptool.com
www.cryptool.de
www.cryptool.es
www.cryptool.pl

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Content (I)
I. CrypTool and Cryptology – Overview
1. Definition and relevance of cryptology
2. The CrypTool project
3. Examples of classical encryption methods
4. Insights from cryptography development
II. CrypTool Features
1. Overview
2. Interaction examples
3. Challenges for developers
III. Examples
1. Encryption with RSA / Prime number test / Hybrid encryption and digital certificates / SSL
2. Digital signature visualized
3. Attack on RSA encryption (small modulus N)
4. Analysis of encryption in PSION 5
5. Weak DES keys
6. Locating key material (“NSA Key”)
7. Attack on digital signature through hash collision search
8. Authentication in a client-server environment
9. Demonstration of a side channel attack (on hybrid encryption protocol) (…)
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Content (II)
III. Examples
10. RSA attack using lattice reduction
11. Random analysis with 3-D visualization
12. Secret Sharing using the Chinese Remainder Theorem (CRT) and Shamir
13. Implementation of CRT in astronomy (solving systems of linear modular equations)
14. Visualization of symmetric encryption methods using ANIMAL
15. Visualizations of AES
16. Visualization of Enigma encryption
17. Visualization of Secure Email with S/MIME
18. Generation of a message authentication code (HMAC)
19. Hash demonstration
20. Educational tool for number theory and asymmetric encryption
21. Point addition on elliptic curves
22. Password quality meter (PQM) and password entropy
23. Brute force analysis
24. Scytale / Rail Fence
25. Hill encryption / Hill analysis
26. CrypTool online help
IV. Project / Outlook / Contact
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Content

I. CrypTool and Cryptology –

Overview
II. CrypTool Features
III. Examples
IV. Project / Outlook / Contact

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Relevance of Cryptography
Examples of Applied Cryptography
 Phone cards, cell phones, remote controls
 Cash machines, money transfer between banks
 Electronic cash, online banking, secure email
 Satellite TV, pay-per-view TV
 Immobilizer systems in cars
 Digital Rights Management (DRM)
 Cryptography is no longer limited to agents, diplomats, and the military.
Cryptography is a modern, mathematically characterized science.
 The breakthrough of cryptography followed the broadening usage
of the Internet
 For companies and governments it is important that systems are secure
and that
users (i.e., clients and employees)
are aware of and understand IT security!
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Definition Cryptology and Cryptography
Cryptology (from the Greek kryptós, "hidden," and lógos, "word") is the science of secure
(or, generally speaking, secret) communication. This security requires that legitimate users,
a transmitter and a receiver, are able to transform information into a cipher by virtue of a key –
that is, a piece of information known only to them. Although the cipher is inscrutable and often
unforgeable to anyone without this secret key, the authorized receiver can either decrypt the
cipher to recover the hidden information or verify that it was sent in all likelihood by someone
possessing the key.

Cryptography was concerned initially with providing secrecy for written messages. Its principles
apply equally well, however, to securing data flow between computers or to encrypting television
signals. Today, the modern (mathematical) science of cryptology is not just a set of encryption
mechanisms. It has since been applied to a broad range of aspects of modern life, including data
and message integrity, electronic signatures, random numbers, secure key exchange, secure
containers, electronic voting, and electronic money.

Source: Britannica (www.britannica.com)

A similar definition can be found on Wikipedia: http://en.wikipedia.org/wiki/Cryptography

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Cryptography – Objectives
 Confidentiality
 Information can be made effectively unavailable or unreadable for
unauthorized individuals, entities, and processes.

 Authentication
 The receiver of a message can verify the identity of the sender.

 Integrity
 Integrity ensures that data has not been altered or destroyed in an
unauthorized manner.

 Non-Repudiation
 The receiver can prove that the message he or she received is precisely what
the sender sent; the sender will have no means to deny any part of his or her
participation.

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The CrypTool Project
 Originated as an awareness program for a large bank (internal training)
 Employee education
 Developed in cooperation with universities (improvement of education)
 Media didactic approach and standard oriented
1998 Project start – over 40 person-years of effort have since been invested
2000 CrypTool available as freeware
2002 CrypTool available on the Citizen’s CD and website of the BSI (German Information Security Agency)
2003 CrypTool becomes open source – hosting by University of Darmstadt (Prof. Eckert)
2007 CrypTool available in German, English, Polish, and Spanish
2008 .NET and Java versions started – hosted by University of Duisburg (Prof. Weis) and SourceForge
2010 CT1 available in fifth language, Serbian; .NET and Java versions to be released
 Awards
2004 TeleTrusT (TTT Förderpreis / Sponsorship Award)
2004 NRW (IT Security Award NRW)
2004 RSA Europe (Finalist of European Information Security Award 2004)
2008 “Selected Landmark” in initiative “Germany – Land of Ideas”
 Developers
 Developed by people from companies and universities in many different countries.
 Currently there are about 50 people working on CrypTool worldwide.
Additional project members or applicable resources are always appreciated.

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Examples of Early Cryptography (1)
Ancient encryption methods

 Tattoo on the shaven head of a slave, concealed by regrown hair

 Atbash (circa 600 B.C.)
- Hebrew secret language, reversed alphabet
 Scytale from Sparta (circa 500 B.C.)
- Described by Greek historian/author Plutarch (45 - 125 B.C.)
- The sender and receiver each need a cylinder (such as a wooden rod) with the same
diameter
- Transposition (plaintext characters are re-sorted)
Encrypted text (ciphertext):
“CSED…”

Plaintext:
“Carl is the
renegade …”

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Examples of Early Cryptography (2)
Caesar encryption (mono-alphabetic substitution cipher)

 Caesar encryption (Julius Caesar, 100 - 44 B.C.)

 Simple substitution cipher

GALLIA EST OMNIS DIVISA ...

Plaintext:

ABCDEFGHIJKLMNOPQRSTUVWXYZ
Secret alphabet:
DEFGHIJKLMNOPQRSTUVWXYZABC

JDOOLD HVW RPQLV GLYLVD ...

 Attack: Frequency analysis (typical character allocation)

Presentation with CrypTool via the following menus:
• Animation: “Indiv. Procedures” \ “Visualization of algorithms” \ “Caesar”
• Implementation: “Crypt/Decrypt” \ “Symmetric (classic)” \ “Caesar / Rot-13”

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Examples of Early Cryptography (3)
Vigenère encryption (poly-alphabetic substitution cipher)

 Vigenère encryption (Blaise de Vigenère, 1523-1596) Keyword character

 Encryption with a keyword using a key table

 Example
Keyword: CHIFFRE
Encrypting: VIGENERE becomes XPOJSVVG
 The plaintext character (V) is replaced by the character in
the corresponding row and in the column of the first
keyword character (c). The next plaintext character (I) is
replaced by the character in the corresponding row and in
the column of the next keyword character (h), and so on.
 If all characters of the keyword have been used, then the
next keyword character is the first key character.
 Attack (via Kasiski test; other tests also exist): Plaintext
combinations with an identical cipher text combination
can occur. The distance of these patterns can be used to
determine the length of the keyword. An additional
frequency analysis can then be used to determine the
key.
Plaintext character Encrypted
character

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Examples of Early Cryptography (4)
Other classic encryption methods

 Homophone substitution
 Playfair (invented 1854 by Sir Charles Wheatstone, 1802-1875)
- Published by Baron Lyon Playfair
- Substitution of one character pair
by another one based on a square-based
alphabet array
 Transfer of book pages
- Adaptation of the One-Time Pad (OTP)
 Turning grille (Fleissner)
 Permutation encryption
- “Double Dice” (double column transposition)
(Pure transposition, but very effective)

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Cryptography in Modern Times
Developments in cryptography from 1870-1970

Classic methods
 are still in use today
(since not everything can be done by a computer…)
 and their principles of transposition and substitution the foundation of the design of
modern algorithms, which combine simpler operations at a bit level (a type of multiple
encryption or cipher cascade), use block ciphers, and/or use repeated uses of an
algorithm over multiple rounds.
Encryption becomes
 more sophisticated,
 mechanized or computerized, and
 remains symmetric.

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Example from the First Half of the 20th Century
Mechanical encryption machines (rotor machines)

Enigma Encryption (Arthur Scherbius, 1878-1929)

 More than 200,000 machines were used in WWII.
 The rotating cylinders encrypt every character of the
text with a new permutation.
 The Polish Cipher Bureau broke the pre-war Enigma
prototype as early as 1932.
 Based on this work, the later Enigma was broken only
with massive effort. About 7000 cryptographers in
the UK used decryption machines, captured Enigma
prototypes, and intercepted daily status reports
(such as weather reports).
 Consequences of the successful cryptanalysis
“The successful cryptanalysis of the Enigma cipher was
a strategic advantage that played a significant role in
winning the war. Some historians assert that breaking
the Enigma code shortened the war by several months
or even a year.”
(translated from http://de.wikipedia.org/wiki/Enigma_%28Machine%29 - March
6, 2006)

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Cryptography – Important Insights (1)
 Kerckhoffs’ principle (first stated in 1883)
‐ Separation of algorithm (method) and key e.g. Caesar encryption:
Algorithm: “Shift alphabet by a certain number of positions to the left”
Key: The “certain number of positions”
‐ Kerckhoffs’ principle:
The secret lies within the key and not within the algorithm;
“security through obscurity” is invalid
 One-Time Pad – Shannon / Vernam
‐ Theoretically completely unbreakable, but highly impractical (used by the red telephone*)
 Shannon’s concepts: Confusion and Diffusion
‐ Relation between M, C, and K should be as complex as possible
(M=message, C=cipher, K=key)
‐ Every ciphertext character should depend on as many plaintext
characters and as many characters of the encryption key as possible
‐ “Avalanche effect” (small modification, big impact)
 Trapdoor function (one-way function)
‐ Fast in one direction, not in the opposite direction (without secret information)
‐ Possessing the secret allows the function to work in the opposite direction
(access to the trapdoor)

CrypTool 1.4.30 * See http://en.wikipedia.org/wiki/Moscow-Washington_hotline Page 15

Examples of Breaches of Kerckhoffs’ Principle
The secret should lie within the key, not in the algorithm

 Cell phone encryption penetrated (December 1999)

“Israeli researchers discovered design flaws that allow the descrambling of supposedly
private conversations carried by hundreds of millions of wireless phones. Alex Biryukov
and Adi Shamir describe in a paper to be published this week how a PC with 128 MB
RAM and large hard drives can penetrate the security of a phone call or data
transmission in less than one second. The flawed algorithm appears in digital GSM
phones made by companies such as Motorola, Ericsson, and Siemens, and used by well
over 100 million customers in Europe and the United States.” *…+
“Previously the GSM encryption algorithms have come under fire for being developed in
secret away from public scrutiny -- but most experts say high security can only come
from published code. Moran [GSM Association] said "it wasn't the attitude at the time to
publish algorithms" when the A5 ciphers was developed in 1989, but current ones being
created will be published for peer review.”
[http://www.wired.com/politics/law/news/1999/12/32900]
 Additional example: In 1999, Netscape Navigator stored email server passwords using
a weak proprietary encryption method.

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Sample of a One-Time Pad Adaptation

Menu:
“Crypt/Decrypt” \
“Symmetric (classic)” \
“Vernam”

Clothes hanger of a Stasi agent

with a secret one-time pad
(source: Spiegel Spezial, 1/1990)

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Key Distribution Problem
Key distribution for symmetric encryption methods

If 2 persons communicate with each other using symmetric encryption,

they need one common secret key.
If n persons communicate with each other, then they need Sn = n * (n-1) / 2 keys.
Number of required keys
That is:
n = 100 persons require
S100 = 4,950 keys; and

Number of keys
n = 1,000 persons require
S1000 = 499,500 keys.

 A factor of 10 more persons means

a factor of 100 more keys.

Number of persons

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Cryptography – Important Insights (2)
Solving the key distribution problem through asymmetric cryptography

Asymmetric cryptography
 For centuries it was believed that the sender and receiver need to know the same secret.
 New idea: Every person needs a key pair (which also solves the key distribution problem)

Asymmetric encryption
 “Everyone can lock a padlock or drop a letter in a mail box.”
 MIT, 1977: Leonard Adleman, Ron Rivest, Adi Shamir (well known as RSA)
 GCHQ Cheltenham, 1973: James Ellis, Clifford Cocks (publicly declassified December 1997)
Key distribution
 Stanford, 1976: Whitfield Diffie, Martin Hellman, Ralph Merkle
(Diffie-Hellman key exchange)
 GCHQ Cheltenham, 1975: Malcolm Williamson

Security in open networks (such as the Internet)

would be extremely expensive and complex without
asymmetric cryptography!
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Performing Encryption and Decryption
Symmetric und asymmetric encryption

Message M C=E(M, KE)

Space
E D M=D(C, KD)

KE KD

Key Space EK Key Space DK

Sender Receiver

secret

a) Symmetric Encryption: KE = KD (e.g. AES)

b) Asymmetric Encryption: KE ≠ KD (e.g. RSA)
public private/secret

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Cryptography – Important Insights (3)
Increasing relevance of mathematics and information technology

 Modern cryptography is increasingly based on mathematics

- There are still new symmetric encryption methods, such as AES; these often feature
better performance and shorter key length compared to asymmetric methods that are
based purely on mathematical problems.
 The security of encryption methods heavily depends on the current state of
mathematics and information technology (IT)
- Computation complexity (meaning processing effort in relation to key length, storage
demand, and data complexity).
 see RSA: Bernstein, TWIRL device, RSA-160, RSA-768 (CrypTool script, chapter 4.11.3)
- Major topics in current research:
Factorization of very large numbers, non-parallelizable algorithms (to counter
quantum computers), protocol weaknesses, random generators, etc.).
 Serious mistake: “Real mathematics has no effects on war.”
(G.H. Hardy, 1940)
 Vendors have realized that security is an essential purchase criterion.

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Demonstration in CrypTool

- Statistic Analysis
- Encrypting twice is not always better:
Caesar: C + D = G (3 + 4 = 7)
Vigenère: - CAT + DOG = FOZ [(2,0,19)+(3,14,6)=(5,14,25)]
- "Hund" + "Katze" ="RUGCLENWGYXDATRNHNMH")
- Vernam (OTP)
- AES (output key, brute-force analysis)

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Content

I. CrypTool and Cryptology –

Overview
II. CrypTool Features
III. Examples
IV. Project / Outlook / Contact

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CrypTool Features eLearning

1. What is CrypTool?
 Freeware program with graphical user interface
 Cryptographic methods can be applied and analysed
 Comprehensive online help (understandable without a deep knowledge of cryptography)
 Contains nearly all state-of-the-art cryptography functions
 Easy entry into modern and classical cryptography
 Not a “hacker tool”

2. Why CrypTool?
 Originated in an awareness initiative of a financial institute
 Developed in close cooperation with universities
 Improvement of university education and in-firm training

3. Target group
 Core group: Students of computer science, business computing, and mathematics
 But also for: computer users, application developers, employees, high school students, etc.
 Prerequisite: PC knowledge
 Preferable: Interest in mathematics and/or programming

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Content of the Program Package
CrypTool program
 All functions integrated in a single program with consistent graphical interface
 Runs on Win32
 Includes cryptography libraries from Secude, cryptovision, and OpenSSL
 Long integer arithmetic from Miracl and GMP, lattice-based reduction via NTL (V. Shoup)
AES Tool
 Standalone program for AES encryption (and creation of self extracting files)
Educational game
 “Number Shark” encourages the understanding of factors and prime numbers.
Comprehensive Online Help (HTML Help)
 Context-sensitive help available via F1 for all program functions (including menus)
 Detailed use cases for most program functions (tutorial)
Script (.pdf file) with background information
 Encryption methods • Prime numbers and factorization • Digital signatures
 Elliptic curves • Public-key certification • Basic number theory • Crypto 2020 • Sage
Two short stories related to cryptography by Dr. C. Elsner
 “The Dialogue of the Sisters” (features an RSA variant as key element)
 “The Chinese Labyrinth” (number theory tasks for Marco Polo)
Learning tool for number theory

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Features (1)
Cryptography Cryptanalysis
Classical cryptography Attack on classical methods
 Caesar (and ROT-13)  Ciphertext only
 Monoalphabetic substitution ‐ Caesar
(and Atbash) ‐ Vigenère (according to Friedman + Schroedel)
 Vigenère ‐ Addition
‐ XOR
 Hill ‐ Substitution
 Homophone substitution ‐ Playfair
 Playfair  Known Plaintext
 ADFGVX ‐ Hill
 Byte Addition ‐ Single-column transposition
 XOR  Manual (program supported)
 Vernam ‐ Mono alphabetical substitution
 Permutation / Transposition (Rail Fence, Scytale, etc.) ‐ Playfair, ADFGVX, Solitaire
 Solitaire Supported analysis methods
Several options to easily comprehend  Entropy, floating frequency
cryptography samples from literature  Histogram, n-gram analysis
 Autocorrelation
 Selectable alphabet  Periodicity
 Options: handling of blanks, etc.  Random analysis
 Base64 / UU-Encode

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Features (2)
Cryptography Cryptanalysis
Modern symmetric encryption Brute-force attack on symmetric algorithms
 IDEA, RC2, RC4, RC6, DES, 3DES, DESX  For all algorithms
 AES candidates of the last selection round  Assumptions:
(Serpent, Twofish, etc.) ‐ Entropy of plaintext is small,
 AES (=Rijndael) ‐ Key is partially known, or
 DESL, DESXL ‐ Plaintext alphabet is known
Asymmetric encryption Attack on RSA encryption
 RSA with X.509 certificates  Factorization of RSA modulus
 RSA demonstration  Lattice-based attacks
‐ For improved understanding of examples
from literature
‐ Alphabet and block length selectable

Hybrid encryption (RSA + AES) Attack on hybrid encryption

 Visualized as an interactive data flow diagram  Attack on RSA, or
 Attack on AES (side-channel attack)

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Features (3)
Cryptography Cryptanalysis
Digital signature Attack on RSA signature
 RSA with X.509 certificates  Factorization of the RSA module
‐ Signature as data flow diagram  Feasible up to 250 bits or 75 decimal
 DSA with X.509 certificates places (on standard desktop PCs)
 Elliptic Curve DSA, Nyberg-Rueppel Attack on hash functions / digital signature
Hash functions  Generate hash collisions for
 MD2, MD4, MD5 ASCII based text (birthday paradox)
 SHA, SHA-1, SHA-2, RIPEMD-160 (up to 40 bits in about five minutes)
Random generators Analysis of random data
 Secude  FIPS-PUB-140-1 test battery
 x2 mod n  Periodicity, Vitányi, entropy
 Linear congruence generator (LCG)  Floating frequency, histogram
 Inverse congruence generator (ICG)  n-gram analysis, autocorrelation
 ZIP compression test

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Features (4)
Visualizations / Demos
 Caesar, Vigenère, Nihilist, DES (all with ANIMAL)
 Enigma (Flash)
 Rijndael/AES (two versions with Flash, one with Java)
 Hybrid encryption and decryption (AES-RSA and AES-ECC)
 Generation and verification of digital signatures
 Diffie-Hellman key exchange
 Secret sharing (with CRT or Shamir)
 Challenge-response method (network authentication)
 Side-channel attack
 Secure email with the S/MIME protocol (with Java and Flash)
 Graphical 3D presentation of (random) data streams
 Sensitivity of hash functions regarding plaintext modifications
 Number theory and RSA cryptosystem (with Authorware)

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Features (5)
Additional functions
 Different functions for RSA and prime numbers
 Homophone and permutation encryption (Double Column Transposition)
 PKCS #12 import and export for PSEs (Personal Security Environment)
 Hash generation of large files (without loading them)
 Flexible brute force attacks on any modern symmetric algorithm
 ECC demonstration (as Java application)
 Password Quality Meter (PQM) and password entropy
 And plenty more…

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Language Structure Analysis
Language analysis options available in CrypTool

Number of characters, n-gram, entropy

 See menu “Analysis” \ “Tools for Analysis” \ ...

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Demonstration of Interactivity (1) Demonstration in
Vigenère analysis CrypTool

The result of the Vigenère analysis can be manually reworked

(changing the key length)
1. Encrypt the sample file with TESTETE
 “Crypt/Decrypt” \ “Symmetric (classic)” \ “Vigenère”
 Enter TESTETE  “Encrypt”
Analysis of the encryption results:
 “Analysis” \ “Symmetric Encryption (classic)” \ “Ciphertext only” \ “Vigenère”
 Derived key length 7, derived key TESTETE

2. Encrypt starting sample with TEST

 “Crypt/Decrypt” \ “Symmetric (classic)” \ “Vigenère”
 Enter TEST  “Encrypt”
Analysis of the encryption results:
 “Analysis” \ “Symmetric Encryption (classic)” \ “Ciphertext only” \ “Vigenère”
 Derived key length 8 – incorrect
 Key length automatically set to 4 (can also be adjusted manually)
 Derived key TEST

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Demonstration of Interactivity (2) Demonstration in
Automated factorization CrypTool

Factorization of a compound number with factorization algorithms

 The algorithms are executed in parallel (multi-threaded)
 Each algorithm has specific advantages and disadvantages; for example, some methods
can only determine small factors

Factorization example 1
48-digit decimal number
316775895367314538931177095642205088158145887517
=
3 * 1129 * 6353 * 1159777 * 22383173213963 * 567102977853788110597

Factorization example 2
75-digit decimal number
2^250 - 1
=
3 * 11 * 31 * 251 * 601 * 1801 * 4051 * 229668251 * 269089806001 * 4710883168879506001 *
5519485418336288303251

Menu:“Indiv. Procedure” \ “RSA Cryptosystem” \ “Factorization of a Number”

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Concepts for a User-Friendly Interface
1. Context sensitive help (F1)
 F1 on a selected menu entry shows information about the algorithm/method.
 F1 in a dialog box explains the usage of the dialog.
 These assistants and the contents of the top menus are cross-linked in the online help.

2. Copying keys to the key entry dialog

 CTRL-V can always be used to paste contents from the clipboard.
 Stored keys can be copied from ciphertext windows via an icon in the dialog. A corresponding
icon in the key entry dialog can be used to paste the key into the key field. CrypTool uses an
internal memory, which is available for every method of the program. (This is particularly
helpful for large “specific” keys, such as in homophone encryption.)

Toolbar Icon

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Challenges for Developers (Examples)
1. Allow additional functions to run in parallel
 Factorization already uses multi-threading to run several algorithms at once
2. High performance
 Locate hash collisions (birthday paradox) or perform brute force analysis
3. Consider memory limits
 In particular with regard to the Floyd algorithm (mappings to locate hash collisions)
and quadratic sieve factorization
4. Time measurement and estimation
 Display remaining time (e.g. while using brute force)
5. Reusability / Integration
 Forms for prime number generation
 RSA cryptosystem (switches the view after successful attack from public key user to
private key owner)
6. Partially automate the consistency of functions, GUI, and online help
(including different languages and the supported Windows OSes: XP, Vista, Win7)

CrypTool 1.4.30 Page 35

Content

I. CrypTool and Cryptology –

Overview
II. CrypTool Features
III. Examples
IV. Project / Outlook / Contact

CrypTool 1.4.30 Page 36

CrypTool Examples
Overview of examples

1. Encryption with RSA / Prime number tests / Hybrid encryption and digital certificates / SSL
2. Digital signature visualized
3. Attack on RSA encryption (small modulus N)
4. Analysis of encryption in PSION 5
5. Weak DES keys
6. Locating key material (“NSA key”)
7. Attack on digital signature through hash collision search
8. Authentication in a client-server environment
9. Demonstration of a side-channel attack (on hybrid encryption protocol)
10. Attack on RSA using lattice reduction
11. Random analysis with 3-D visualization
12. Secret Sharing using the Chinese Remainder Theorem (CRT) and Shamir
13. Implementation of CRT in astronomy (solving systems of linear modular equations)
14. Visualization of symmetric encryption methods using ANIMAL
15. Visualizations of AES
16. Visualization of Enigma encryption
17. Visualization of Secure Email with S/MIME
18. Generation of a message authentication code (HMAC)
19. Hash demonstration
20. Educational tool for number theory and asymmetric encryption
21. Point addition on elliptic curves
22. Password quality meter (PQM) and password entropy
23. Brute force analysis
24. Scytale / Rail Fence
25. Hill encryption / Hill analysis
26. CrypTool online help

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Examples (1)
Encryption with RSA

 Basis of the SSL protocol (access to protected websites), among others

 Asymmetric encryption using RSA
 Every user has a key pair – one public and one private key.
 Sender encrypts with public key of the recipient.
 Recipient decrypts with his or her private key.
 Usually implemented in combination with symmetric methods (hybrid
encryption): the symmetric key is transmitted using RSA asymmetric
encryption/decryption Key pair


Confidential
Encryption  Decryption
Confidential
Message  Message


Public Key Private Key

Sender uses public key Recipient uses his or

of the recipient her private key
CrypTool 1.4.30 Page 38
Examples (1)
Encryption using RSA – Mathematical background / algorithm

 Public key: (n, e) [the modulus N is often capitalized]

 Private key: (d)
where
p, q are large, randomly chosen prime numbers with n = p*q;
d is calculated under the constraints gcd[(n),e] = 1; e*d ≡ 1 mod (n).
Encryption and decryption operation: (m e)d ≡ m mod n
• n is the modulus, whose length in bits is referred to as the key length of a given
RSA implementation.
• gcd = greatest common divisor.
• (n) is Euler’s totient function.

Procedure
 Transform the message into its binary representation
 Encrypt message blockwise such that m = m1,...,mk where for all mj: 0  mj < n;
The maximum block size r should be chosen such that 2 r  n (and 2r-1 < n)

CrypTool 1.4.30 Page 39

Examples (1)
Prime number tests – RSA requires the use of very large primes

 Fast probabilistic tests

 Deterministic tests

The prime number test

methods can test whether a
large number is prime much
faster than the known
factorization methods can
divide a number of similar size
into its prime factors.

For the AKS test the GMP

library (GNU Multiple Precision
Arithmetic Library) was
integrated into CrypTool.
Menu: “Indiv. Procedure” \ “RSA Cryptosystem” \
“Prime Number Test”
Remark: 2^255 - 1 = 7 * 31 * 103 * 151 * 2143 * 11119 * 106591 * 131071 * 949111 *
9520972806333758431 * 5702451577639775545838643151

CrypTool 1.4.30 Page 40

Examples (1)
Hybrid encryption and digital certificates

 Hybrid encryption – combination of asymmetric and symmetric encryption

1. Generation of a random symmetric key (session key)
2. Session key is transferred – protected by asymmetric key
3. Message is transferred – protected by session key
 Problem: man-in-the-middle attacks – does the public key of the recipient
really belong to the recipient?
 Solution: digital certificates – a central instance (e.g., GlobalSign, Telesec,
VeriSign, Deutsche Bank PKI), trusted by all users, ensures the authenticity
of the certificate and the associated public key (similar to a passport issued
by a national government).
 Hybrid encryption based on digital certificates is the foundation for all
secured electronic communication
 Internet shopping and online banking
 Secure email

CrypTool 1.4.30 Page 41

Examples (1)
Secured online connection using SSL and certificates

This means that the connection is

authenticated (at least on one side)
and that the transferred data is strongly
encrypted.
CrypTool 1.4.30 Page 42
Examples (1)
Attributes / fields of a certificate

General attributes / fields

 Issuer (e.g., VeriSign)
 Requestor
 Validity period
 Serial number
 Certificate type / version (X.509v3)
 Signature algorithm
 Public key (and method)

Public Key

CrypTool 1.4.30 Page 43

Examples (1)
Establishing a secure SSL connection (server authentication)

Client Server
1. SSL initiation

Send server certificate 2.

3. Validate server certificate (using locally installed root certificates)

4. Retrieve public key of server (from server certificate)

5. Generate a random symmetric key (session key)

6. Send session key

(encrypted with public key of server)

Receive session key 7.

(decrypted by private key of the server)

Encrypted communication based on

exchanged session key

CrypTool 1.4.30 Page 44

Examples (1)
Establishing a secure SSL connection (server authentication)

General
 The example shows the typical SSL connection establishment in order to transfer
sensitive data over the internet (e.g. online shopping).
 During SSL connection establishment only the server is authenticated using a digital
certificate (authentication of the user usually occurs through user name and password
after the SSL connection has been established).
 SSL also offers the option for client authentication based on digital certificates.
Remarks on establishing an SSL connection (see previous slide)
 Step 1: SSL Initiation – the characteristics of the session key (e.g. bit size)
as well as the symmetric encryption algorithm (e.g. 3DES, AES) are negotiated.
 Step 2: In a multi-level certificate hierarchy, the required intermediate certificates
are also passed to the client.
 Step 3: The root certificates installed in the browser’s certificate store are used to
validate the server certificate.
 Step 5: The session key is based on the negotiated characteristics (see step 1).

CrypTool 1.4.30 Page 45

Examples (2)
Digital signature visualized

Digital signature
 Increasingly important
‐ Equivalent to a handwritten signature
(digital signature law)
‐ increasingly used by companies,
governments, and consumers
 Few actually know how it works

Visualization in CrypTool
 Interactive data flow diagram
 Similar to the visualization of hybrid
encryption

Menu: “Digital Signatures/PKI” \

“Signature Demonstration (Signature Generation)”

CrypTool 1.4.30 Page 46

Examples (2)
Digital signature visualized: a) Preparation

2. Provide key and

1. Select hash function certificate (not shown here)

CrypTool 1.4.30 Page 47

Examples (2)
Digital signature visualized: b) Cryptography

3. Calculate 3. 4. 5.
hash value
4. Encrypt
hash value
with private
key (sign)
5. Generate
signature

CrypTool 1.4.30 Page 48

Examples (2)
Digital signature visualized: c) Result

6. The signed document can

now be saved.

The operations can be performed in

any order as long as the necessary
data for each step is available.

CrypTool 1.4.30 Page 49

Examples (3)
Attack on RSA encryption with short RSA modulus

Example from Song Y. Yan, Number Theory for Computing, Springer, 2000
 Public key
‐ RSA modulus N = 63978486879527143858831415041 (95 bits, 29 decimal digits)
‐ public exponent e = 17579
To perform the actual
 Ciphertext (block length = 8):
cryptanalysis (revealing the
C1 = 45411667895024938209259253423,
private key), the ciphertext
C2 = 16597091621432020076311552201,
C3 = 46468979279750354732637631044, is not actually necessary!
C4 = 32870167545903741339819671379
 This text must be deciphered!
Solution using CrypTool (further details in the examples section of the online help)
 Enter public parameters into “RSA cryptosystem” (menu: “Indiv. Procedures”)
 Clicking the button “Factorize the RSA modulus” yields the two prime factors pq = N
 Based on that information the private exponent d=e-1 mod (p-1)(q-1) can be determined
 Decrypt the ciphertext with d: Mi = Cid mod N
In CrypTool, this attack is only practical for RSA key sizes up to about 250 bits.
A successful attack means you could then digitally sign in someone else’s name!
CrypTool 1.4.30 Page 50
Examples (3)
Short RSA modulus: Enter public RSA parameters

Menu: “Indiv. Procedures” \ “RSA Cryptosystem” \ “RSA Demonstration …”

1.Enter RSA
parameters N and e

2. Factorize

CrypTool 1.4.30 Page 51

Examples (3)
Short RSA modulus: Factorize RSA modulus

3. Factorization
yields p and q

CrypTool 1.4.30 Page 52

Examples (3)
Short RSA modulus: Determine private key d

Change the view

to the owner of the
secret key

4. p and q have
been entered
automatically,
and secret key d
has been calculated

5. Change settings

CrypTool 1.4.30 Page 53

Examples (3)
Short RSA modulus: Change settings

6. Select alphabet

7. Select coding method

8. Select block length

CrypTool 1.4.30 Page 54

Examples (3)
Short RSA modulus: Decrypt ciphertext

9. Enter ciphertext

10. Decrypt

CrypTool 1.4.30 Page 55

Examples (4)
Analysis of encryption used in the PSION 5

Practical application of cryptanalysis

Attack on the encryption option in the
PSION 5 PDA word processing application

Starting point: an encrypted file on the PSION

Requirements
 Encrypted English or German text
 Depending on method and key length, text of at least 100 bytes up to several kB
Procedure
 Pre-analysis
 entropy
 floating entropy probably classical
 compression test encryption algorithm
 Auto-correlation
 Automated analysis with classical methods

CrypTool 1.4.30 Page 56

Examples (4)
PSION 5 PDA – determine entropy, compression test

Compressibility:
not indicative; a larger
value would be a clear
indication of weak
cryptography

Entropy: not all possible

values are present, but
does not indicate a specific
encryption method.

CrypTool 1.4.30 Page 57

Examples (4)
PSION 5 PDA – determine auto-correlation

Distinctive comb pattern:

typical for Vigenère,
XOR, and byte addition

* The encrypted file is available in CrypTool (see CrypTool\examples\psion2-EN.hex).

CrypTool 1.4.30 Page 58

Examples (4)
PSION 5 PDA – automatic analysis

Automatic analysis using

 Vigenère: no success
 XOR: no success
 Byte addition
 CrypTool calculates the key length
using auto-correlation: 32 bytes
 The user can choose which character
is expected to occur most frequently:
the empty space = 0x20 (ASCII code)
 Analysis calculates the most likely
key (based on assumptions
regarding distribution)
 Result: good, but not perfect

CrypTool 1.4.30 Page 59

Examples (4)
PSION 5 PDA – results of automatic analysis

Results of automatic analysis under the assumption of “byte addition”

 Result is good, but not perfect: 25 out of 32 key bytes correct.
 The key length 32 was correctly determined.

 The password entered was not 32 bytes long.

 PSION Word derives the actual key from the password.
 Manual post-processing produces the encrypted text (not shown).

CrypTool 1.4.30 Page 60

Examples (4)
PSION 5 PDA – determining the remaining key bytes

First, copy the key to the clipboard during automatic analysis.

Then, in the automatic analysis hex dump:
 Determine incorrect byte positions, e.g. 0x1C at position 8
 Guess and write down corresponding correct bytes: “a” = 0x61
Next, in the encrypted initial file hex dump:
 Determine initial bytes from the calculated byte positions: 0x8D
 Calculate correct key bytes with CALC.EXE: 0x8D - 0x61 = 0x2C
Finally, get the key from the clipboard:
 Correct 12865B341498872C393E437413DBA456B123A3111ED9BFB705D313E72D4B8E95
 Decrypt encrypted initial document using byte addition
 Bytes at position 3, 3+32, 3+2*32, etc. are now correct

CrypTool 1.4.30 Page 61

Examples (5)
Weak DES key

Encrypting twice with this key

returns the plaintext.

CrypTool 1.4.30 Page 62

Examples (6)
Locate key material

The function “Floating frequency” is suitable for locating key

material and encrypted areas in files.
Background
 Key data is “more random” than text or program code
 Can be recognized as peaks in the “floating frequency”
 Example: the “NSA key” in advapi32.dll (Windows NT)

CrypTool 1.4.30 Page 63

Examples (6)
Floating frequency comparison

CrypTool 1.4.30 Page 64

Examples (7)
Attack on digital signatures

Attack
Find two
messages with
the same hash
value!

Menu: “Analysis” \ “Hash” \ “Attack on the Hash Value of the Digital Signature”

CrypTool 1.4.30 Page 65

Examples (7)
Attack on digital signature – idea (I)

Attack on the digital signature of an ASCII text by means of a hash collision search.

Idea:
 ASCII texts can be modified by changing/inserting non-printable characters without
changing the visible content
 Modify two texts in parallel until a hash collision is found
 Exploit the birthday paradox (birthday attack)
 Generic attack applicable to all hash functions
 Can parallelized across many machines (not implemented in CrypTool)
 Implemented in CrypTool as part of the bachelor thesis
“Methods and Tools for Attacks on Digital Signatures” (German), 2003.

Concepts :
 Mappings
 Modified Floyd algorithm (constant memory consumption)

CrypTool 1.4.30 Page 66

Examples (7)
Attack on digital signature – idea (II)

1. Modification: starting from a message M

1. 3. create N different messages M1, ..., MN
with the same “content” as M.
harmless 2. Search: find modified messages MiH and
message M H Compare Identical MjS with the same hash value.
2. hashes signatures
3. Attack: the signatures of those two
documents MiH and MjS are the same.
1. 3
.
evil message M S

We know from the birthday paradox that for hash values of bit length n:
 search collision between MH and M1S, ..., MNS : N  2n
 search collision between M1H, ..., MNH and M1S, ..., MNS : N  2n/2

Estimated number of generated messages in order

to find a hash collision.

CrypTool 1.4.30 Page 67

Locate Hash Collisions (1)
Mapping via text modifications

Randomly selected starting point for collisions search

Identical
hash value

hash

hash
modify
0011
1111 modify

1100 1100
0010 0010 1110
0100 1111
0010

modify hash
modify
0010
0100

harmless evil
message message  green / red: path from a tree to the cycle – this can lead to a useful or useless
collision, respectively.
 square / round: hash value has even / odd parity, respectively
 black: all nodes within the cycle

CrypTool 1.4.30 Page 68

Locate Hash Collisions (2)
Floyd Algorithm: meet within the cycle

start / collision Example:

cycle
Function graph with
increment 1
increment 2
32 nodes

Starting point
Step 1: Locate matching point within cycle:
• Two series with identical starting point [16]:
one series with increment 1, the other with
increment 2.
• Result s(based on graph theory):
- both series always end up in a cycle.
- both series match in a node within the cycle
(in this case 0).

CrypTool 1.4.30 Page 69

Locate Hash Collisions (3)
Step into cycle (extension of Floyd): find entry point

start / collision
cycle
move in sub tree
move in cycle

Entry point

Step 2: Locate entry point of series 1 in the

cycle [25]:
• Series 1 starts again from starting point;
series 3 with an increment of 1 starts at
matching point within the cycle (in this
case 0).
• Result: The series (1 and 3) match in
cycle entry point of series 1 (in this case
25)
• The predecessors (in this case 17 and 2)
result in a hash collision.

CrypTool 1.4.30 Page 70

Birthday Paradox Attack on Digital Signature

Examination of Floyd algorithm

 Visual and interactive presentation
of the Floyd algorithm (“Moving
through the mapping” into a
cycle).
 Adaptation of the Floyd algorithm
for a digital signature attack.

Starting point
Good collision
Bad collision
*The Floyd algorithm is implemented in CrypTool, but the
visualization of the algorithm has not yet been implemented.

CrypTool 1.4.30 Page 71

Examples (7)
Attack on digital signature

An example of a “good” mapping

(nearly all nodes are green).
In this graph almost all nodes
belong to a big tree, which leads
into the cycle with an even hash
value and where the entry point
predecessor within the cycle is
odd. That means that the attacker
finds a useful collision for nearly all
starting points.
good collision

Page 72
Examples (7)
Attack on digital signature: attack

1.

2.

4. 3.

Menu: “Analysis” \ “Hash” \ “Attack on the Hash Value of the Digital Signature”

CrypTool 1.4.30 Page 73

Examples (7)
Attack on digital signature: results

Experimental results
 A 72-bit partial collision (i.e., the
MD5: 4F 47 DF 1F first 72 hash value bits are
D2 DE CC BE 4B 52
86 29 F7 A8 1A 9A
identical) was found in a couple of
days using a single PC.
 Today, signatures with hash values
of 128 bits or less are vulnerable
MD5: 4F 47 DF 1F to a massive parallel search!
30 38 BB 6C AB 31
B7 52 91 DC D2 70  It is therefore recommended to
use hash values with a length of at
The first 32 bits of the hash values are identical. least 160 bits.

In addition to the interactive tool, CrypTool also includes a command-line feature to

execute and log the results for entire sets of parameter configurations.

CrypTool 1.4.30 Page 74

Examples (8)
Authentication in a client-server environment

 Interactive demo for

different authentication
methods.
 Specifies vulnerabilities
that an attacker could
take advantage of.
 Allows the user to play
the role of an attacker.
 Learning outcome:
Only mutual
authentication is secure.

Menu: “Indiv. Procedures” \ “Protocols” \ “Network Authentication”

CrypTool 1.4.30 Page 75

Examples (9)
Demonstration of a side-channel attack (on a hybrid encryption protocol)

Menu: “Analysis” \ “Asymmetric Encryption” \ “Side-Channel Attack on Textbook RSA”

CrypTool 1.4.30 Page 76

Examples (9)
Side channel attack concept

Ulrich Kuehn: “Side-channel attacks on textbook RSA and ElGamal encryption”, 2003
Prerequisites [CCA (Chosen-ciphertext attack) against deciphering oracle]
 RSA encryption: C = Me (mod N) and decryption: M = Cd mod N.
 128-bit session keys (in M) are encoded according to textbook RSA (null padding).
 The server knows the secret key d and
– uses after decryption only the least significant 128 bits without validating the null-padded bits, meaning that the
server does not recognize if there is something there other than zero.
– An error message is prompted if the encryption attempt results in an “incorrect” session key (decrypted text
cannot be interpreted by the server). In all other cases there will be no message.
Idea for attack: Approximation of Z in 129 bits from the equation N = M * Z per M = ⌊|N/Z|⌋

M= 000...................................000 Session Key C = Me (mod N)

Null-Padding
M
All bit positions for Z are successively calculated: for each step the attacker gets one additional bit. He or she
then modifies C to C’ (see below). If a bit overflow occurs while calculating M’ on the server (recipient), the
server sends an error message. Based on this information, the attacker can determine a single bit of Z.

If and only if the most significant bit of M is equal to 1, then M’ is not equal to M mod 2128.

M’ = Session Key 000...............000 Session Key C’ = M’e = Me.(1+Z.2128)e (mod N)

M.Z.2128 M

CrypTool 1.4.30 Page 77

Examples (10)
Mathematics: Attacks on RSA using lattice reduction

 Demonstrates that the parameters

of RSA should be chosen to
withstand the lattice reduction
attacks described in current
literature.
 3 variants which are not resistant:
1. The secret exponent d is too small in
comparison to N.
2. One of the factors of N is partially
known.
3. A part of the plaintext is known.
 These assumptions are realistic.

Menu: “Analysis” \
“Asymmetric Encryption” \
“Lattice Based Attacks on RSA” \ …

CrypTool 1.4.30 Page 78

Examples (11)
Random analysis with 3-D visualization

3-D visualization for random analysis

Example 1
 Open an arbitrary file (e.g. report in Word or PowerPoint
presentation)
 It is recommended to select a file with at least 100 kB
 3-D analysis using menu: “Analysis” \ “Analyze Randomness” \
“3-D Visualization”
 Result: structures are easily recognizable

Example 2
 Generation of random numbers: “Indiv. Procedures” \ “Tools”
\ “Generate Random Numbers”
 It is recommended to generate at least 100,000 random bytes
 3-D analysis using menu: “Analysis” \ “Analyze Randomness” \
“3-D Visualization”
 Result: uniform distribution (no structures are recognizable)

CrypTool 1.4.30 Page 79

Examples (12)
Secret sharing with CRT – implementation of the Chinese remainder theorem (CRT)

Secret sharing example (1)

 Problem
 5 people each receive a single key
 To gain access, at least 3 of the 5 people must be
present
 “Options” allows the user to configure
additional settings.

 “Calc. steps” shows all of the steps in key

generation.

Menu: “Indiv. Procedures” \

“Chinese Remainder Theorem Applications” \
“Secret Sharing by CRT”

CrypTool 1.4.30 Page 80

Examples (12)
Shamir secret sharing

Secret sharing example (2)

 Problem
• A secret value is to be divided among n
people.
• t out of n people are required to restore
the secret value K.
• (t, n) threshold scheme
 Menu: “Indiv. Procedures” \ “Secret Sharing
Demonstration (Shamir)”
1. Enter the secret K, number of persons n
and threshold t
2. Generate polynomial
3. Select parameters
 Click “Reconstruction” to restore the secret.

CrypTool 1.4.30 Page 81

Examples (13)
Implementation of CRT to solve linear modular equation systems

Astronomical scenario
 How long would it take for
a given number of planets
(with different rotation
times) to become aligned?
 The result is a linear
modular equation system
that can be solved with the
Chinese remainder theorem
(CRT).
 In this demo you can enter
up to 9 equations and
compute a solution using
the CRT.

Menu: “Indiv. Procedures” \ “Chinese Remainder Theorem Applications” \

“Astronomy and Planetary Motion”

CrypTool 1.4.30 Page 82

Examples (14)
Visualization of symmetric encryption methods using ANIMAL (1)

Animated visualization of several Animation speed Scaling of visualization

symmetric algorithms
 Caesar
 Vigenère
 Nihilist
 DES

CrypTool
 Menu: “Indiv. Procedures” \ “Visualization
of Algorithms” \ …
 Interactive animation control using
integrated control center window.

Animation controls (next,

forward, pause, etc.)

Direct selection of an animation step

CrypTool 1.4.30 Page 83

Examples (14)
Visualization of symmetric encryption methods using ANIMAL (2)

Visualization of DES encryption

After the permutation of the input block with The core function f of DES, which links the right
the initialization vector (IV), the key K is half of the block Ri-1 with the partial key Ki.
permuted with PC1 and PC2.

CrypTool 1.4.30 Page 84

Examples (15)
Visualizations of AES (Rijndael cipher) – in Flash

Rijndael Animation (the Rijndael cipher was the winner of the AES selection competition)
 Shows the encryption processes of each round (using fixed initial data)
Rijndael Inspector
 Test with your own data (shows the contents of the matrix after each round)

Menu: “Indiv. Procedures” \ “Visualization of Algorithms” \ “AES” \ “Rijndael Animation” or “Rijndael Inspector”

CrypTool 1.4.30 Page 85

Examples (15)
Flow visualization of AES (Rijndael Cipher) – in Java

Rijndael flow visualization

 Visualization of data changes per round using color gradient

Menu: “Indiv. Procedures” \ “Visualization of Algorithms” \ “AES” \ “Rijndael Flow Visualization…”

CrypTool 1.4.30 Page 86

Examples (16)
Visualization of the Enigma encryption

Select rotors

Change rotor
setting
Change plugs

Show
settings

Input of
plaintext Reset Enigma
to initial
Output of state or
encrypted text random state
Additional HTML online help
CrypTool 1.4.30 Page 87
Examples (17)
Visualization of secure Email using S/MIME

S/MIME visualization
 Control Center: Sign/Encrypt messages with different parameters
 Animation: From the sender’s creation of the message until it is read by the receiver

Menu: “Indiv. Procedures” \ “Protocols” \ “Secure E-Mail with S/MIME…”

CrypTool 1.4.30 Page 88

Examples (18)
Generation of a Keyed-Hash Message Authentication Code (HMAC)

Keyed-Hash Message Authentication

Code (HMAC)
 Ensures
‐ Integrity of a message
‐ Authentication of the message
 Basis: a common key for sender
and recipient
2.
 Alternative: Digital signature 1.
3.
Generation of a MAC in CrypTool
1. Choose a hash function
2. Select HMAC variant
3. Enter a key (or keys,
depending on the HMAC variant) 4.
4. Generation of the HMAC (automatic)
Menu: “Indiv. Procedures” \ “Hash” \ “Generation of HMACs”

CrypTool 1.4.30 Page 89

Examples (19)
Hash demonstration

Sensitivity of hash functions to plaintext

modifications
1. Select a hash function
2. Modify characters in plaintext 1.

Example: 2.
By adding a space after the word “CrypTool”
in the example text, 50.6 % of the bits in the
resulting hash value will change.

A good hash function should react highly

sensitively to even the smallest change in the
plaintext – “Avalanche effect” (small change,
big impact).

Menu: “Indiv. Procedures” \ “Hash” \

“Hash Demonstration”

CrypTool 1.4.30 Page 90

Examples (20)
Educational tool for number theory

 Number theory
supported by graphical
elements and
interactive tools
 Topics
1. Integers
2. Residue classes
3. Prime generation
4. Public-key
cryptography
5. Factorization
6. Discrete logarithms

Menu: “Indiv. Procedures” \ “Number Theory – Interactive” \

“Learning tool for number theory”

CrypTool 1.4.30 Page 91

Examples (21)
Point addition on elliptic curves

 Visualization of point addition on elliptic curves

 Foundation of elliptic curve cryptography (ECC)

Example 1
 Mark point P on the curve
 Mark point Q on the curve
 Press button “P+Q”: the straight line through
P and Q intersects the curve at point -R
 Mirroring -R over the X-axis produces the
point R

Example 2
 Mark point P on the curve
 Press button “2*P”: the tangent of point P
intersects the curve at point -R
 Mirroring -R over the X-axis produces the
point R
Change curve parameters Delete points Log file of
calculations
Menu: “Indiv. Procedures” \ “Number Theory –
Interactive” \ “Point Addition on Elliptic Curves”

CrypTool 1.4.30 Page 92

Examples (22)
Password Quality Meter (PQM) (1)

Functions
 Measure the quality of passwords
 Compare with PQMs in other applications: KeePass, Mozilla und PGP
 Experimental evaluation with the CrypTool algorithm
 Example: Input of a password in cleartext
Password: 1234 Password: X40bTRds&11w_dks

Menu: “Indiv. Procedures” \ “Tools” \ “Password Quality Meter” Menu: “Indiv. Procedures” \ “Tools” \ “Password Entropy”

CrypTool 1.4.30 Page 93

Examples (22)
Password Quality Meter (PQM) (2)

Insights from the Password Quality Meter

 Password quality depends primarily on the length of the password.
 A higher quality of the password can be achieved by using different types of characters:
upper/lower case, numbers, and special characters (password space)
 Password entropy is an indicator of the randomness of the password characters within
the password space (higher password entropy results in improved password quality)
 Passwords should not exist in a dictionary (remark: a dictionary check is not yet
implemented in CrypTool).
Quality of a password from an attacker’s perspective
 Attack on a password (if any number of attempts are possible):
1. Classical dictionary attack
2. Dictionary attack with variants (e.g., 4-digit number combinations: “Summer2007”)
3. Brute-force attack by testing all combinations (with additional parameters such as limitations
on the types of character sets)
 A good password should be chosen so that attacks 1 and 2 do not compromise the
password. Regarding brute-force attacks, the most important factors are the length of
the password (recommended at least 8 characters) and the character set that was used.
CrypTool 1.4.30 Page 94
Examples (23)
Brute-force analysis (1)

Brute-force analysis
Optimized brute-force analysis with the assumption that the key is partially known.

Example – Analysis with DES (ECB)

Attempt to find the remainder of the key in order to decrypt an encrypted text.
(Assumption: the plaintext is a block of 8 ASCII characters.)

Key (Hex) Encrypted text (Hex)

68ac78dd40bbefd* 66b9354452d29eb5
0123456789ab**** 1f0dd05d8ed51583
98765432106***** bcf9ebd1979ead6a
0000000000****** 8cf42d40e004a1d4
000000000000**** 0ed33fed7f46c585
abacadaba******* d6d8641bc4fb2478
dddddddddd****** a2e66d852e175f5c

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Examples (23)
Brute-force analysis (2)

1. Input of encrypted text Select “View” \ “Show as HexDump”

2. Use brute-force analysis

3. Input partially known key
4. Start brute-force analysis
5. Analysis of the results: the correct decryption usually has relatively low entropy. However, because a very short
plaintext has been used in this example, the correct result does not have the lowest entropy.

Menu: “Analysis” \ “Symmetric Encryption (modern)” \ “DES (ECB)”

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Examples (24)
Scytale / Rail Fence

Scytale and Rail Fence

 Transpositions scramble the order of letters in the
cleartext

Transposition variant
 Number of edges (Scytale)
 Number of rows (Rail Fence)
 Offset

Text options
 General text options (Menu: “Options” \ “Text Options…”)
 Formatting options for cleartext and ciphertext
 Processing of upper/lower case
 Alphabet for text processing (i.e., what set of
characters should be encrypted/decrypted)
 Return to the default settings by clicking the “Restore
Standard” button
Menu: “Crypt/Decrypt” \ “Symmetric (classic)” \ “Scytale / Rail Fence…”

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Examples (25)
Hill encryption / Hill analysis (1)

Hill encryption
 Polygraphic substitution cipher
 Based on linear algebra

Key
 Alphabet characters (see text options)
or number values
 Enter or generate random key
 Select multiplication variant
 Size of matrix
 Hill options

Menu:
“Crypt/Decrypt” \
“Symmetric (classic)” \
“Hill …”

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Examples (25)
Hill encryption / Hill analysis (2)

Hill encryption
 Sample text with key LVMH

Hill analysis (with known plaintext)

1. Long plaintext/ciphertext
 Select plaintext (startingexample-en.txt)
 Select ciphertext
(Hill encryption of <startingexample-en.txt>)
 Click “Continue” to search for the key

2. Reduced plaintext/ciphertext
 Clear all of the plaintext except the first word
(“CrypTool”)
 Clear all of the ciphertext except for the first eight
characters (“PnhdJovl”)
 Click “Continue” to reveal the key!
Which length of plaintext/ciphertext is required to find
the correct encryption key?
Menu: “Analysis” \ “Symmetric Encryption (classic)” \ “Known Plaintext” \ “Hill…”

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Examples (26)
CrypTool online help (1)

Menu: “Help” \ “Starting Page”

CrypTool 1.4.30 Page 100

Examples (26)
CrypTool online help (2)

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Examples (26)
CrypTool online help (3)

CrypTool 1.4.30 Page 102

Content

I. CrypTool and Cryptology –

Overview
II. CrypTool Features
III. Examples
IV. Project / Outlook / Contact

CrypTool 1.4.30 Page 103

Future CrypTool Development (1)
Examples of what is planned after the release of CrypTool 1.4.30 (see readme for details)
CT1 FIPS test with the ability to analyze packets with lengths other than 2500 bytes, etc.
CT1 = CrypTool 1.x
JCT Tri-partite key agreements
JCT Visualization of the interoperability between S/MIME and OpenPGP formats
JCT Entropy analysis New versions:
JCT Fleissner grille, Autokey Vigenère, interactive cryptanalysis of classic ciphers CT2 = CrypTool 2.0
JCT Analysis of transposition ciphers using the ACO algorithm
JCT Visualization of zero-knowledge proofs JCT = JCrypTool
JCT Visualization of Quantum Key Agreement, BB84 protocol (both introduced on the
JCT Action history with the ability to create and replay any given cipher cascade next slides)
CT2 Comprehensive visualization on the topic of prime numbers
CT2 Encryption and automated cryptanalysis of the Enigma machine (and possibly of Sigaba as well)
CT2 Cube attack (I. Dinur and A. Shamir: “Cube Attacks on Tweakable Black Box Polynomials”, 2008)
CT2 Demonstration of Bleichenbacher’s RSA signature forgery
CT2 Demonstration of virtual credit card numbers (as an educational tool against credit card abuse)
CT2 WEP encryption and WEP analysis
CT2 Mass pattern search
CT2 Distributed cryptanalysis
CT2 Demonstration of SOA security (SOAP messages with WS-Security)
CT2 Framework to create and analyze LFSR stream ciphers
CT2 Graphical design-oriented mode for beginners and detailed mode for experts
CT2/JCT Creation of a command-line interface for batch processing
CT2/JCT Modern pure plugin architecture with plugin reloading capability
All Expanded parameterization and flexibility of present algorithms
Ideas Visualization of the SSL protocol // Demonstration of visual cryptography

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Future CrypTool Development (2)
In Progress: the two successor versions of CT v1 (see readme file)
1. JCT: Port and redesign of CrypTool in Java / SWT / Eclipse 3.6 / RCP
 see: http://jcryptool.sourceforge.net
 Release Candidate RC2 is available since May 2010.
2. CT2: Port and redesign of the C++ version with C# / WPF / VS2010 / .NET 4.0
 direct successor of current release: allows visual programming, etc.
 Download from: http://cryptool2.vs.uni-due.de/index.php?page=14&lm=1&ql=4
 Beta 3 is available since July 2010 (since July 2008, betas are continuously updated).

CrypTool 2 (CT2) JCrypTool (JCT)

CrypTool 1.4.30 Page 105
Future CrypTool Development (3)

CrypTool 2 (CT2) JCrypTool (JCT)

CrypTool 1.4.30 Page 106
CrypTool as a Framework
Proposal
 Reuse the comprehensive set of algorithms, included libraries, and interface elements
as a foundation.
 Free training to help get started with CrypTool development.
 Advantage: code written for university theses or other projects will not simply disappear,
but rather be further maintained.

Current development environment for CT1: Microsoft Visual Studio C++ , Perl,
Subversion Source Code Management
 CrypTool 1.4.30: Visual C++ .NET (= VC++ 9.0)(= Visual Studio 2008 Standard)
 Description for developers: see readme-source.txt
 Sources and binaries of release versions are available for download.
To get sources of current betas, please see the Subversion repository.

Development environments for CT2 and JCT

 CT2 – C# version: .NET with Visual Studio 2010 Express Edition (free) and WPF
 Java – Java version: Eclipse 3.6, RCP, SWT (free)

CrypTool 1.4.30 Page 107

CrypTool – Request for Contribution
Every contribution to the project is highly appreciated
 Feedback, criticism, suggestions, and ideas
 Integration of additional algorithms, protocols, analysis (consistency and completeness)
 Development assistance (programming, layout, translation, testing)
 For the current C/C++ project
 For the new projects (preferred):
‐ C# project: “CrypTool 2.0” = CT2
‐ Java project: “JCrypTool” = JCT
 In particular, university faculties that use CrypTool for educational purposes are invited to
contribute to the further development of CrypTool.
 Samples of open tasks are on the following developer pages:
‐ CT2: See the list http://cryptool2.vs.uni-due.de/, Volunteer, Open Tasks
‐ JCT: See the wiki http://sourceforge.net/apps/mediawiki/jcryptool/index.php?title=CurrentDevelopment
 Users that make a significant contributions can request to be referenced by name in the online
help, the readme file, the about dialog, and/or on the CrypTool website.
 CrypTool v1 is currently being downloaded over 6000 times per month from the CrypTool website.
Just over half of these downloads are of the English version. The betas of the two successors are
already being downloaded over 1000 times a month each.

CrypTool 1.4.30 Page 108

CrypTool – Summary
THE e-learning program for cryptology
Successfully active as an open-source project for over ten years
Over 300,000 total downloads
Widespread international usage in schools, universities, companies,
and government agencies
Extensive online help and documentation
Available for free
Multilingual

CrypTool 1.4.30 Page 109

Contact
Prof. Bernhard Esslinger

University of Siegen
Faculty 5, Economics and Business Computing
Deutsche Bank AG
Director, IT Security Manager

[email protected]

www.cryptool.org
www.cryptool.com
www.cryptool.de
www.cryptool.es
www.cryptool.pl

Additional contacts: See readme within the CrypTool folder

CrypTool 1.4.30 Page 110

Additional Literature
As an introduction to cryptology – and more

 Klaus Schmeh, “Codeknacker gegen Codemacher. Die faszinierende Geschichte der

Verschlüsselung”, 2nd edition, 2007, W3L [German]
 Simon Singh, “The Codebook”, 1999, Doubleday
 Johannes Buchmann, “Introduction to Cryptography”, 2nd edition, 2004, Springer
 Paar / Pelzl: “Understanding Cryptography – A Textbook for Students and Practitioner”, 2009,
Springer
 [HAC] Menezes / van Oorschot / Vanstone, “Handbook of Applied Cryptography”, 1996, CRC
Press
 Van Oorschot / Wiener, “Parallel Collision Search with Application to Hash Functions and Discrete
Logarithms”, 1994, ACM
 Antoine Joux, “Algorithmic Cryptanalysis”, 2009, Chapman & Hall/CRC Cryptography and
Network Security Series
 Additional cryptography literature – see also the links at the CrypTool web page and the
literature in the CrypTool online help (e.g. by Wätjen, Salomaa, Brands, Schneier, Shoup,
Stamp/Low, etc.)
 Importance of cryptography in the broader context of IT security and risk management
 See e.g. Kenneth C. Laudon / Jane P. Laudon / Detlef Schoder, “Wirtschaftsinformatik”, 2nd edition, 2009,
Pearson, chapter 15 about IT Security [German]
 Wikipedia: http://en.wikipedia.org/wiki/Risk_management
 CrypTool site: http://cryptool.com/index.php/en/cryptool-for-awareness-aboutmenu-74.html

CrypTool 1.4.30 Page 111

www.cryptool.org / .com / .de / .es / .pl

CrypTool 1.4.30 Page 112

www.cryptool-online.org
CrypTool-Online is the
newest member in the
family of CrypTool
related websites:
• CrypTool site (CT1)
• CT2 developer site
• JCT developer site
• CryptoPortal for
teachers (currently
only in German)
• CrypTool-Online
(experiment with
cryptography from
within your browser)

CrypTool 1.4.30 Page 113

www.cryptoportal.org

The teacher’s portal is

currently only available in
German. We would greatly
welcome any help with an
English version.

CrypTool 1.4.30 Page 114

Downloads: Software and the CrypTool Script

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