Applied Cryptography For Pentesting

Encoding and Cryptography

Encoding is often confused with encryption and hashing. They are not the same. But before I go into the differences, I'll first mention how they relate:
  1. All three transform data into another format.
  2. Both encoding and encryption are reversible, and hashing is not.
Symmetric/Asymmetric Encryption  

Asymmetric encryption works by exploiting very difficult mathematical problems with back doors that enable a fast solution to the problem, if you have a small piece of very important data. The usual mathematical problems are factoring large numbers and discrete logarithms. Asymmetric algorithms work on a fixed data size, typically 1024-2048 bits for RSA and El Gamal, and 384 bits for Elliptic Curve versions of RSA or El Gamal. (Elliptic Curve versions use a different field than the integers for their computations. RSA and El Gamal and similar systems work with any field that specifies both a multiply and an add operation, and ECC has a different representation of that field that magically packs 'more' data into a bit. It's a super clever way of making well-known mechanisms fit into less memory, and my one-sentence introduction can't begin to do it justice. The simplicity is the amazing part.)

Symmetric encryption works by mixing secret input with a secret key in such a fashion that it is (a) fast (b) cannot derive the input or key from the output. The details of the mixing varies significantly.

Difference Between Stream/Block Cipher

  • A typical stream cipher encrypts plaintext one byte at a time, although a stream cipher may be designed to operate on one bit at a time or on units larger than a byte at a time.
  • A block cipher encrypts one block at a time. The block may be of size one byte or more or less. That means we can also encrypt a block of one byte by help of a stream cipher as a stream.
Data Encryption Standard (DES)

DES is the archetypal block cipher — an algorithm that takes a fixed-length string of plaintext bits and transforms it through a series of complicated operations into another ciphertext bitstring of the same length. In the case of DES, the block size is 64 bits. DES also uses a key to customize the transformation, so that decryption can supposedly only be performed by those who know the particular key used to encrypt. The key ostensibly consists of 64 bits; however, only 56 of these are actually used by the algorithm. Eight bits are used solely for checking parity, and are thereafter discarded. Hence the effective key length is 56 bits, and it is always quoted as such.

Triple DES (3DES)

In cryptographyTriple DES (3DES) is the common name for the Triple Data Encryption Algorithm (TDEA or Triple DEAsymmetric-key block cipher, which applies the Data Encryption Standard (DES) cipher algorithm three times to each data block. Triple DES uses a "key bundle" that comprises three DES keys, K1, K2 and K3, each of 56 bits (excluding parity bits). 

The encryption algorithm is: ciphertext = EK3(DK2(EK1(plaintext)))

i.e., DES encrypt with K1, DES decrypt with K2, then DES encrypt with K3.

Decryption is the reverse: plaintext = DK1(EK2(DK3(ciphertext)))

i.e., decrypt with K3, encrypt with K2, then decrypt with K1.

Each triple encryption encrypts one block of 64 bits of data. In each case the middle operation is the reverse of the first and last. This improves the strength of the algorithm when using keying option 2, and provides backward compatibility with DES with keying option 3.

Advanced Encryption Standard (AES) 

AES is based on a design principle known as a substitution-permutation network, combination of both substitution and permutation, and is fast in both software and hardware. Unlike its predecessor DES, AES does not use a Feistel network. AES is a variant of Rijndael which has a fixed block size of 128 bits, and a key size of 128, 192, or 256 bits. By contrast, the Rijndael specification per se is specified with block and key sizes that may be any multiple of 32 bits, both with a minimum of 128 and a maximum of 256 bits.Key lengths: 128, 192 and 256 bits.


In cryptography, RC4 is the most widely used software stream cipher and is used in popular protocols such as Transport Layer Security (TLS) (to protect Internet traffic) and WEP (to secure wireless networks). RC4 generates a pseudorandom stream of bits (a keystream). As with any stream cipher, these can be used for encryption by combining it with the plaintext using bit-wise exclusive-or; decryption is performed the same way (since exclusive-or with given data is an involution). (This is similar to the Vernam cipher except that generated pseudorandom bits, rather than a prepared stream, are used.). Key size must be in the range of 40–2,048 bits.


In cryptography, SHA-1 is a cryptographic hash function designed by the United States National Security Agency and is a U.S. Federal Information Processing Standard published by the United States NIST. SHA-1 produces a 160-bit (20-byte) hash value. A SHA-1 hash value is typically rendered as a hexadecimal number, 40 digits long.

Message digest size: 160 bits

For a hash function for which L is the number of bits in the message digest, finding a message that corresponds to a given message digest can always be done using a brute force search in approximately 2 in the power of L evaluations. This is called a preimage attack and may or may not be practical depending on L and the particular computing environment.


The MD5 message-digest algorithm was a widely used cryptographic hash function producing a 128-bit (16-byte) hash value, typically expressed in text format as a 32 digit hexadecimal number. MD5 has been utilized in a wide variety of cryptographic applications, and is also commonly used to verify data integrity. MD5 was designed by Ron Rivest in 1991 to replace an earlier hash function, MD4.

The source code in RFC 1321 contains a "by attribution" RSA license.  In 2004 it was shown that MD5 is not collision resistant. As such, MD5 is not suitable for applications like SSL certificates or digital signatures that rely on this property for digital security. Also in 2004 more serious flaws were discovered in MD5, making further use of the algorithm for security purposes questionable.
In December 2008, a group of researchers used this technique to fake SSL certificate validity, and CMU Software Engineering Institute now says that MD5 "should be considered cryptographically broken and unsuitable for further use", and most U.S. government applications now require the SHA-2 family of hash functions. In 2012, the Flame malware exploited the weaknesses in MD5 to fake a Microsoft digital signature.


In cryptography, a keyed-hash message authentication code (HMAC) is a specific construction for calculating a message authentication code (MAC) involving a cryptographic hash function in combination with a secret cryptographic key. As with any MAC, it may be used to simultaneously verify both the data integrity and the authentication of a message. Any cryptographic hash function, such as MD5 or SHA-1, may be used in the calculation of an HMAC; the resulting MAC algorithm is termed HMAC-MD5 or HMAC-SHA1 accordingly. The cryptographic strength of the HMAC depends upon the cryptographic strength of the underlying hash function, the size of its hash output, and on the size and quality of the key.

An iterative hash function breaks up a message into blocks of a fixed size and iterates over them with a compression function. For example, MD5 and SHA-1 operate on 512-bit blocks. The size of the output of HMAC is the same as that of the underlying hash function (128 or 160 bits in the case of MD5 or SHA-1, respectively), although it can be truncated if desired. HMAC-SHA1 and HMAC-MD5 are used within the IPsec and TLS protocols.