The speed of exhaustive key searches against DES after 1990 began to cause discomfort amongst

users of DES. However, users did not want to replace DES as it takes an enormous amount of
time and money to change encryption algorithms that are widely adopted and embedded in large
security architectures.

The pragmatic approach was not to abandon the DES completely, but to change the manner in
which DES is used. This led to the modified schemes of Triple DES (sometimes known as
3DES).

Incidentally, there are two variants of Triple DES known as 3-key Triple DES (3TDES) and 2-
key Triple DES (2TDES).

3-KEY Triple DES

Before using 3TDES, user first generate and distribute a 3TDES key K, which consists of three
different DES keys K1, K2 and K3. This means that the actual 3TDES key has length 3×56 = 168
bits. The encryption scheme is illustrated as follows −

The encryption-decryption process is as follows −

 Encrypt the plaintext blocks using single DES with key K1.
 Now decrypt the output of step 1 using single DES with key K2.
  Finally, encrypt the output of step 2 using single DES with key K3.
 The output of step 3 is the ciphertext.
 Decryption of a ciphertext is a reverse process. User first decrypt using K3, then encrypt
with K2, and finally decrypt with K1.

Due to this design of Triple DES as an encrypt–decrypt–encrypt process, it is possible to use a

3TDES (hardware) implementation for single DES by setting K1, K2, and K3 to be the same value.
This provides backwards compatibility with DES.

Second variant of Triple DES (2TDES) is identical to 3TDES except that K3is replaced by K1. In
other words, user encrypt plaintext blocks with key K1, then decrypt with key K2, and finally
encrypt with K1 again. Therefore, 2TDES has a key length of 112 bits.

Triple DES systems are significantly more secure than single DES, but these are clearly a much
slower process than encryption using single DES.

In cryptography, Triple DES (3DES), officially the Triple Data Encryption Algorithm
(TDEA or Triple DEA), is a symmetric-key block cipher, which applies the Data Encryption
Standard (DES) cipher algorithm three times to each data block.

The original DES cipher's key size of 56 bits was generally sufficient when that algorithm was
designed, but the availability of increasing computational power made brute-force attacks
feasible. Triple DES provides a relatively simple method of increasing the key size of DES to
protect against such attacks, without the need to design a completely new block cipher algorithm.

Contents
 1 Definitive standards
 2 Name of the algorithm
 3 Algorithm
 4 Keying options
o 4.1 Other terms
 5 Encryption of more than one block
 6 Security
 7 Usage
 8 See also
 9 References and notes
 10 External links

Definitive standards
The Triple Data Encryption Algorithm (TDEA) is defined in each of:
  ANS[1] X9.52-1998 Triple Data Encryption Algorithm Modes of Operation [2] (withdrawn)
 FIPS PUB 46-3 Data Encryption Standard (DES)[3] (does not include keying options) (withdrawn[4])

 NIST Special Publication 800-67 Revision 1 Recommendation for the Triple Data Encryption
Algorithm (TDEA) Block Cipher[5]

 ISO/IEC 18033-3:2010: Part 3: Block ciphers [6]

Name of the algorithm

The earliest standard that defines the algorithm (ANS X9.52, published in 1998) describes it as
the "Triple Data Encryption Algorithm (TDEA)" — i.e. three operations of the Data Encryption
Algorithm specified in ANSI X3.92 — and does not use the terms "Triple DES" or "DES" at all.
FIPS PUB 46-3 (1999) defines the "Triple Data Encryption Algorithm (TDEA)", but also uses
the terms "DES" and "Triple DES". It uses the terms "Data Encryption Algorithm" and "DES"
interchangeably, including starting the specification with:

The Data Encryption Standard (DES) shall consist of the following Data Encryption Algorithm
(DES) [sic] and Triple Data Encryption Algorithm (TDEA, as described in ANSI X9.52).

NIST SP 800-67 (2004,[7] 2012) primarily uses the term TDEA, but also refers to "Triple DES
(TDEA)". ISO/IEC 18033-3 (2005) uses "TDEA", but mentions that:

The TDEA is commonly known as Triple DES (Data Encryption Standard).

While none of the standards that define the algorithm use the term "3DES", this term is used by
some vendors, users, and cryptographers.[8][9][10][11]

Algorithm
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.

Keying options
The standards define three keying options:

Keying option 1

All three keys are independent.

Keying option 2

K1 and K2 are independent, and K3 = K1.

Keying option 3

All three keys are identical, i.e. K 1 = K2 = K3.

Keying option 1 is the strongest, with 3 × 56 = 168 independent key bits.

Keying option 2 provides less security, with 2 × 56 = 112 key bits. This option is stronger than
simply DES encrypting twice, e.g. with K1 and K2, because it protects against meet-in-the-middle
attacks.

Keying option 3 is equivalent to DES, with only 56 key bits. It provides backward compatibility
with DES, because the first and second DES operations cancel out. It is no longer recommended
by the National Institute of Standards and Technology (NIST),[5] and is not supported by
ISO/IEC 18033-3.

Each DES key is nominally stored or transmitted as 8 bytes, each of odd parity,[12] so a key
bundle requires 24 bytes for option 1, 16 for option 2, or 8 for option 3.

Other terms

"Keying option n" is the term used by the standards (X9.52, FIPS PUB 46-3, SP 800-67,
ISO/IEC 18033-3) that define the TDEA. However, other terms are used in other standards and
related recommendations, and general usage.

 For keying option 1:

o 3TDEA, in NIST SP 800-57[13] and SP 800-78-3[14]
o Triple-length keys, in general usage [15][16]

 For keying option 2:

o 2TDEA, in NIST SP 800-57[13] and SP 800-78-3[14]
 o Double-length keys, in general usage[15][16]

Encryption of more than one block

As with all block ciphers, encryption and decryption of multiple blocks of data may be
performed using a variety of modes of operation, which can generally be defined independently
of the block cipher algorithm. However, ANS X9.52 specifies directly, and NIST SP 800-67
specifies via SP 800-38A[17] that some modes shall only be used with certain constraints on them
that do not necessarily apply to general specifications of those modes. For example, ANS X9.52
specifies that for cipher block chaining, the initialization vector shall be different each time,
whereas ISO/IEC 10116[18] does not. FIPS PUB 46-3 and ISO/IEC 18033-3 define only the
single block algorithm, and do not place any restrictions on the modes of operation for multiple
blocks.

Security
In general, Triple DES with three independent keys (keying option 1) has a key length of 168
bits (three 56-bit DES keys), but due to the meet-in-the-middle attack, the effective security it
provides is only 112 bits.[13] Keying option 2 reduces the effective key size to 112 bits (because
the third key is the same as the first). However, this option is susceptible to certain chosen-
plaintext or known-plaintext attacks,[19][20] and thus, it is designated by NIST to have only 80 bits
of security.[13]

The best attack known on keying option 1 requires around 232 known plaintexts, 2113 steps, 290
single DES encryptions, and 288 memory[21] (the paper presents other tradeoffs between time and
memory). This is not currently practical and NIST considers keying option 1 to be appropriate
through 2030.[13] If the attacker seeks to discover any one of many cryptographic keys, there is a
memory-efficient attack which will discover one of 228 keys, given a handful of chosen plaintexts
per key and around 284 encryption operations.[22]

Usage
The electronic payment industry uses Triple DES and continues to develop and promulgate
standards based upon it (e.g. EMV).[23]

Microsoft OneNote,[24] Microsoft Outlook 2007[25] and Microsoft System Center Configuration
Manager 2012[26] use Triple DES to password protect user content and system data.