Exploring Cryptography Using CrypTool
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1 NEMATYC 2018 Exploring Cryptography Using CrypTool Valeria D Orazio Massachusetts Maritime Academy
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3 Importance of Cryptography
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5 1998 Project start Originated as an internal business application for information security training for employees of a large German bank. Developed in cooperation with universities (improvement of education) Over 50 volunteer developers worldwide contribute to the program CrypTool becomes open source
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7 E-Learning Software: CrypTool 1 runs under Windows 1998 CrypTool 2 runs under Windows 2011 JCrypTool (JCT) runs under Linux, Mac and Windows 2011 CrypTool-Online International crypto cipher challenge "MTC3" Additional Website available on
8 CrypTool-Online is the online version of the e-learning program CrypTool. CrypTool-Online allows to try out different algorithms in a browser / smartphone. Experiment with the introduced methods in an interactive way directly on the website.
9 CrypTool 1 is available in 6 languages German, English, Spanish, Polish, Serbian and Greek. CrypTool 1 The current version of CrypTool 1 offers among other things: Numerous classic and modern cryptographic algorithms (encryption and decryption, key generation, secure passwords, authentication, secure protocols, etc.) Visualization of several algorithms (Caesar, RSA, Diffie-Hellman, digital signatures, AES, etc.) Cryptanalysis of several algorithms (Vigenère, RSA, AES, etc.) Related auxiliary methods (primality tests, factorization, base64 encoding, etc.) Number theory tutorial Comprehensive online help
10 CrypTool 2 is the modern successor of CrypTool 1. CrypTool 2 provides a graphical user interface for visual programming. So workflows can be visualized and controlled to enable intuitive manipulation and interaction of cryptographic functions. CrypTool 2 provides a greater variety of cryptanalytical tools to analyze or even break classical and modern ciphers. For instance, it is possible to apply a ciphertext-only attack on an Enigma-encrypted ciphertext.
11 JCrypTool is an open-source e-learning platform, developed to not only let everybody experiment with cryptography, but to develop and extend the JCrypTool platform in various ways with their own crypto plug-ins.
12 Mystery Twister C3 is an international Crypto Cipher Contest offering more than 200 challenges, a moderated forum and an ongoing hall-of-fame. Mystery Twister C3 is available in English and German
13 The CrypTool Portal -> Documentation CT Book CT Presentations
14 Some International 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
15 CrypTool in scientific papers Teaching Cryptology At All Levels Using CrypTool R.Yang, L. Wallace, I. Burchett Proceedings of the 15 th Colloquium for information Systems Security Education Fairborn, Ohio June13-15, 2011 An Interactive and Collaborative Approach to Teaching Cryptology S. Adamovic, M.Sarac, M.Veinovic, M. Milosavljevic and A.Jevremovic Journal of Educational Technology & Society Vol. 17, No. 1, Game Based Learning for 21st Century Transferable Skills: Challenges and Opportunities (January 2014), pp Cryptool 2 in Teaching Cryptography Major K.Loussios Journal of Computations & Modelling, vol.4, no.1, 2014, ISSN: (print), (online) Scienpress Ltd, 2014 Visualization of the Avalanche Effect in CT2, Camilo Echeverri Thesis Bachelor of Science Wirtschaftsinformatik Reducing the complexity of understanding cryptology using CrypTool, S. Hick, B. Esslinger, and A.Waker
16 Usability of Cryptool Event Schuelerkrypto ( Student Crypto) in Germany Reducing the complexity of understanding cryptology using CrypTool, S. Hick, B. Esslinger, and A.Waker The 10th International Conference on Education and Information Systems,Technologies and Applications (EISTA 2012), Orlando, Florida, USA, (17-20 July 2012)
17 Classical Cipher A cipher is the set of instructions for encrypting or decrypting a message
18 Cryptanalysis: science of studying attacks against cyphertexts.
19 Classical Cyphers A classical cipher was used from 2000 B.C. in Egypt to World War II, before computers become available.. Plaintext is viewed as a sequence of elements (e.g., bits or characters) Substitution cipher: replacing each element of the plaintext with another element (Caesar, Vigenère, Hill). Transposition (or permutation) cipher: rearranging the order of the elements of the plaintext (Scytale, Rail fence). Product cipher: using multiple stages of substitutions and transpositions (ADFG(V)X).
20 Caesar Cipher Caesar cipher is a type of substitution cipher in which each letter in the plaintext is replaced by a letter some fixed number (Key) of positions down the alphabet. Monoalphabetic cipher: fixed substitution over the entire message Cipher Wheel
21 Cryptanalysis of the Caesar Cipher Brute-Force Attack: only 26 possible keys Character Frequencies: Letter Frequency for English Letters
22 Modular (Clock) Arithmetic MOD MOD MOD MOD 26
23 Vigenère Cipher Vigenère Cipher is a polyalphabetic substitution first published in To encrypt, a table of alphabets can be used, called a tabula recta or Vigenère square, that consists of several Caesar ciphers in sequence with different shift values. A keyword is then used to choose which ciphertext alphabet to use.
24 The Vigenère square
25 Cryptanalysis of Vigenère Cipher Kasiski Method (1863): use repetitions in ciphertext to give clues about the length of the keyword, looking for same plaintext an exact period apart, leading to same ciphertext. The Friedman test (1920): uses the index of coincidence, The Incidence of Coincidence is the probability that two randomly selected letters are the same. i.e. it measures variation of the cipher letter frequencies. Plaintext: TOBEORNOTTOBE Key: NOWNOWNOWNOWN Ciphertext: GCXRCNACPGCXR Since repeats are 9 chars apart, guess period is 3 or 9 Solving Vigenère Cipher: 1. Use Kasiski method & IC to estimate the length of the key word, d. 2. Separate ciphertext into d sections, and solve each as a monoalphabetic cipher.
26 Hill cipher Hill cipher is a polygraphic substitution cipher based on linear algebra (1929). Key: Invertible n n matrix -> gcd (d,26)=1 Plaintext and Ciphertext: n x m matrix C Key P (mod 26) P Key 1 * C (mod 26) Hill's cipher machine which performed a 6 6 matrix multiplication modulo 26 using a system of gears and chains.
27 I 2x2 = d=11 gcd (26,d)=1 P = C Y R P P = CRYPTOOL T O O L = C = * = MOD 26 C = U N U L R S I X = UNULRISX
28 I 2x2 8 1 MOD 26 P = * = MOD 26 P = C R Y P T O O L = CRYPTOOL
29 Cryptanalysis of Hill Cipher known plaintext ciphertext: the key can be recovered solving a system of linear equations C Key P (mod 26) a b = c d * a + 17b = 20
30 frequency analysis: for very long ciphertexts, frequency analysis may be useful when applied to bigrams (for a 2 by 2 hill cipher) The most common English digraphs in order of frequency: TH, HE, AN, IN, ER, ON, RE, ED, ND, HA, AT, EN, ES, OF, NT, EA, TI, TO, IO, LE, IS, OU, AR, AS, DE, RT, VE Guess: C Key P (mod 26) 19 7 = Key 7 4 MOD 26 P 1 = Key = * MOD 26? If it is not, try other combinations of common ciphertext digrams until we get something that is correct.
31 t h f t h e z m = Key MOD 26 P 1 = Key = * MOD 26
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