Triple DES explained

Triple Data Encryption Algorithm
Publish Date:1981
Derived From:DES
Key Size:112 or 168 bits
Block Size:64 bits
Structure:Feistel network
Rounds:48 DES-equivalent rounds
Cryptanalysis:Lucks: 232 known plaintexts, 2113 operations including 290 DES encryptions, 288 memory; Biham: find one of 228 target keys with a handful of chosen plaintexts per key and 284 encryptions

In cryptography, Triple DES (3DES or TDES), officially the Triple Data Encryption Algorithm (TDEA or Triple DEA), is a symmetric-key block cipher, which applies the DES cipher algorithm three times to each data block. The 56-bit key of the Data Encryption Standard (DES) is no longer considered adequate in the face of modern cryptanalytic techniques and supercomputing power; Triple DES increases the effective security to 112 bits. A CVE released in 2016, CVE-2016-2183, disclosed a major security vulnerability in the DES and 3DES encryption algorithms. This CVE, combined with the inadequate key size of 3DES, led to NIST deprecating 3DES in 2019 and disallowing all uses (except processing already encrypted data) by the end of 2023.[1] It has been replaced with the more secure, more robust AES.

While US government and industry standards abbreviate the algorithm's name as TDES (Triple DES) and TDEA (Triple Data Encryption Algorithm),[2] RFC 1851 referred to it as 3DES from the time it first promulgated the idea, and this namesake has since come into wide use by most vendors, users, and cryptographers.[3] [4] [5]

History

In 1978, a triple encryption method using DES with two 56-bit keys was proposed by Walter Tuchman; in 1981, Merkle and Hellman proposed a more secure triple-key version of 3DES with 112 bits of security.[6]

Standards

The Triple Data Encryption Algorithm is variously defined in several standards documents:

Algorithm

The original DES cipher's key size of 56 bits was considered generally sufficient when it 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.

A naive approach to increase the strength of a block encryption algorithm with a short key length (like DES) would be to use two keys

(K1,K2)

instead of one, and encrypt each block twice:

EK2(EK1(rm{plaintext}))

. If the original key length is

n

bits, one would hope this scheme provides security equivalent to using a key

2n

bits long. Unfortunately, this approach is vulnerable to the meet-in-the-middle attack: given a known plaintext pair

(x,y)

, such that

y=EK2(EK1(x))

, one can recover the key pair

(K1,K2)

in

2n+1

steps, instead of the

22n

steps one would expect from an ideally secure algorithm with

2n

bits of key.

Therefore, 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:

rm{ciphertext}=EK3(DK2(EK1(rm{plaintext}))).

That is, encrypt with

K1

, decrypt with

K2

, then encrypt with

K3

.

Decryption is the reverse:

rm{plaintext}=DK1(EK2(DK3(rm{ciphertext}))).

That is, 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. Sometimes known as 3TDEA[15] or triple-length keys.[16]

    This is the strongest, with 3 × 56 = 168 independent key bits. It is still vulnerable to the meet-in-the-middle attack, but the attack requires 22 × 56 steps.

    Keying option 2
  • K1 and K2 are independent, and K3 = K1. Sometimes known as 2TDEA[15] or double-length keys.[16]

    This provides a shorter key length of 56*2 or 112 bits and a reasonable compromise between DES and keying option 1, with the same caveat as above.[17] This is an improvement over "double DES" which only requires 256 steps to attack. NIST disallowed this option in 2015.[15]

    Keying option 3
  • All three keys are identical, i.e. K1 = K2 = K3.

    This is backward-compatible with DES, since two of the operations cancel out. ISO/IEC 18033-3 never allowed this option, and NIST no longer allows K1 = K2 or K2 = K3.

    Each DES key is 8 odd-parity bytes, with 56 bits of key and 8 bits of error-detection.[8] A key bundle requires 24 bytes for option 1, 16 for option 2, or 8 for option 3.

    NIST (and the current TCG specifications version 2.0 of approved algorithms for Trusted Platform Module) also disallows using any one of the 64 following 64-bit values in any keys (note that 32 of them are the binary complement of the 32 others; and that 32 of these keys are also the reverse permutation of bytes of the 32 others), listed here in hexadecimal (in each byte, the least significant bit is an odd-parity generated bit, which is discarded when forming the effectively 56-bit key): 01.01.01.01.01.01.01.01, FE.FE.FE.FE.FE.FE.FE.FE, E0.FE.FE.E0.F1.FE.FE.F1, 1F.01.01.1F.0E.01.01.0E, 01.01.FE.FE.01.01.FE.FE, FE.FE.01.01.FE.FE.01.01, E0.FE.01.1F.F1.FE.01.0E, 1F.01.FE.E0.0E.01.FE.F1, 01.01.E0.E0.01.01.F1.F1, FE.FE.1F.1F.FE.FE.0E.0E, E0.FE.1F.01.F1.FE.0E.01, 1F.01.E0.FE.0E.01.F1.FE, 01.01.1F.1F.01.01.0E.0E, FE.FE.E0.E0.FE.FE.F1.F1, E0.FE.E0.FE.F1.FE.F1.FE, 1F.01.1F.01.0E.01.0E.01, 01.FE.01.FE.01.FE.01.FE, FE.01.FE.01.FE.01.FE.01, E0.01.FE.1F.F1.01.FE.0E, 1F.FE.01.E0.0E.FE.01.F1, 01.FE.FE.01.01.FE.FE.01, FE.01.01.FE.FE.01.01.FE, E0.01.01.E0.F1.01.01.F1, 1F.FE.FE.1F.0E.FE.FE.0E, 01.FE.E0.1F.01.FE.F1.0E, FE.01.1F.E0.FE.01.0E.F1, E0.01.1F.FE.F1.01.0E.FE, 1F.FE.E0.01.0E.FE.F1.01, 01.FE.1F.E0.01.FE.0E.F1, FE.01.E0.1F.FE.01.F1.0E, E0.01.E0.01.F1.01.F1.01, 1F.FE.1F.FE.0E.FE.0E.FE, 01.E0.01.E0.01.F1.01.F1, FE.1F.FE.1F.FE.0E.FE.0E, E0.1F.FE.01.F1.0E.FE.01, 1F.E0.01.FE.0E.F1.01.FE, 01.E0.FE.1F.01.F1.FE.0E, FE.1F.01.E0.FE.0E.01.F1, E0.1F.01.FE.F1.0E.01.FE, 1F.E0.FE.01.0E.F1.FE.01, 01.E0.E0.01.01.F1.F1.01, FE.1F.1F.FE.FE.0E.0E.FE, E0.1F.1F.E0.F1.0E.0E.F1, 1F.E0.E0.1F.0E.F1.F1.0E, 01.E0.1F.FE.01.F1.0E.FE, FE.1F.E0.01.FE.0E.F1.01, E0.1F.E0.1F.F1.0E.F1.0E, 1F.E0.1F.E0.0E.F1.0E.F1, 01.1F.01.1F.01.0E.01.0E, FE.E0.FE.E0.FE.F1.FE.F1, E0.E0.FE.FE.F1.F1.FE.FE, 1F.1F.01.01.0E.0E.01.01, 01.1F.FE.E0.01.0E.FE.F1, FE.E0.01.1F.FE.F1.01.0E, E0.E0.01.01.F1.F1.01.01, 1F.1F.FE.FE.0E.0E.FE.FE, 01.1F.E0.FE.01.0E.F1.FE, FE.E0.1F.01.FE.F1.0E.01, E0.E0.1F.1F.F1.F1.0E.0E, 1F.1F.E0.E0.0E.0E.F1.F1, 01.1F.1F.01.01.0E.0E.01, FE.E0.E0.FE.FE.F1.F1.FE, E0.E0.E0.E0.F1.F1.F1.F1, 1F.1F.1F.1F.0E.0E.0E.0EWith these restrictions on allowed keys, Triple DES was reapproved with keying options 1 and 2 only. Generally, the three keys are generated by taking 24 bytes from a strong random generator, and only keying option 1 should be used (option 2 needs only 16 random bytes, but strong random generators are hard to assert and it is considered best practice to use only option 1).

    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,[18] 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[19] 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. 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,[20] [21] and thus it is designated by NIST to have only 80 bits of security. This can be considered insecure; as a consequence, Triple DES's planned deprecation was announced by NIST in 2017.[22]

    The short block size of 64 bits makes 3DES vulnerable to block collision attacks if it is used to encrypt large amounts of data with the same key. The Sweet32 attack shows how this can be exploited in TLS and OpenVPN.[23] Practical Sweet32 attack on 3DES-based cipher-suites in TLS required

    236.6

    blocks (785 GB) for a full attack, but researchers were lucky to get a collision just after around

    220

    blocks, which took only 25 minutes.

    OpenSSL does not include 3DES by default since version 1.1.0 (August 2016) and considers it a "weak cipher".[24]

    Usage

    As of 2008, the electronic payment industry uses Triple DES and continues to develop and promulgate standards based upon it, such as EMV.[25]

    Earlier versions of Microsoft OneNote,[26] Microsoft Outlook 2007[27] and Microsoft System Center Configuration Manager 2012[28] use Triple DES to password-protect user content and system data. However, in December 2018, Microsoft announced the retirement of 3DES throughout their Office 365 service.[29]

    Firefox and Mozilla Thunderbird[30] use Triple DES in CBC mode to encrypt website authentication login credentials when using a master password.

    Implementations

    Below is a list of cryptography libraries that support Triple DES:

    Some implementations above may not include 3DES in the default build, in later or more recent versions.

    See also

    Notes and References

    1. Web site: Barker . Elaine . Roginsky . Allen . 2019-03-01 . Transitioning the use of cryptographic algorithms and key lengths . 2022-09-20 . https://web.archive.org/web/20190511203915/https://nvlpubs.nist.gov/nistpubs/SpecialPublications/NIST.SP.800-131Ar2.pdf . 2019-05-11 . live . Gaithersburg, MD . NIST Publications . NIST SP 800-131A Revision 2 . 7 . 10.6028/nist.sp.800-131ar2.
    2. Web site: Triple DES Encryption. IBM. 2010-05-17.
    3. 1003.4085. New Comparative Study Between DES, 3DES and AES within Nine Factors. Journal of Computing. 2. 3. March 2010. 2151-9617. 2010arXiv1003.4085A. Alanazi. Hamdan. O.. Zaidan. B. B.. Zaidan. A. A.. Jalab. Hamid A.. Shabbir. M.. Al-Nabhani. Y..
    4. Web site: Cisco PIX 515E Security Appliance Getting Started Guide: Obtaining a DES License or a 3DES-AES License. https://web.archive.org/web/20160207205956/http://instrumentation.obs.carnegiescience.edu/FourStar/Documents/FourStar%20Commercial%20Manuals/CISCO%20PIX%20515E/PIX%20515E%20Getting%20Started%20Guide.pdf . 2016-02-07 . live. 2006. Cisco. 2017-09-05.
    5. Web site: 3DES Update: Most Banks Are Done, But.... https://web.archive.org/web/20130510231256/http://www.highbeam.com/doc/1G1-161420739.html. dead. 2013-05-10. ATM & Debit News. 2007-03-29. 2017-09-05.
    6. Merkle, R. and M. Hellman, "On the Security of Multiple Encryption", Communications of the ACM, vol. 24, no. 7, pp. 465–467, July 1981.
    7. The ESP Triple DES Transform. 1851. P.. Karn. P.. Metzger. W.. Simpson. September 1995.
    8. Web site: ANSI X9.52-1998 Triple Data Encryption Algorithm Modes of Operation . subscription. 2017-09-05. Extends ANSI X3.92-1981 Data Encryption Algorithm.
    9. Notice of Withdrawal: ANS at least 10 years past approval date. 2008-11-14. 39. 46. 5. ANSI Standards Action. ANSI. https://web.archive.org/web/20170906134039/https://share.ansi.org/Shared%20Documents/Standards%20Action/2008%20PDFs/SAV3946.pdf . 2017-09-06 . live. 2017-09-05. 0038-9633.
    10. Web site: FIPS PUB 46-3: Data Encryption Standard (DES). https://web.archive.org/web/20030405225406/http://csrc.nist.gov/publications/fips/fips46-3/fips46-3.pdf . 2003-04-05 . live. Oct 25, 1999. United States Department of Commerce. 2017-09-05.
    11. Announcing Approval of the Withdrawal of Federal Information Processing Standard (FIPS) 46–3..... https://web.archive.org/web/20080917125417/http://csrc.nist.gov/groups/STM/cmvp/documents/05-9945-DES-Withdrawl.pdf . 2008-09-17 . live. Federal Register. 70. 96. 2005-05-19. 2017-09-05.
    12. Web site: NIST Special Publication 800-67 Revision 2: Recommendation for the Triple Data Encryption Algorithm (TDEA) Block Cipher. Elaine. Barker. Nicky. Mouha. NIST. November 2017. 10.6028/NIST.SP.800-67r2. free. 2017-11-21. https://web.archive.org/web/20171201131807/https://nvlpubs.nist.gov/nistpubs/SpecialPublications/NIST.SP.800-67r2.pdf. 2017-12-01. live.
    13. NIST to Withdraw Special Publication 800-67 Revision 2 https://csrc.nist.gov/news/2023/nist-to-withdraw-sp-800-67-rev-2
    14. Web site: ISO/IEC 18033-3:2010 Information technology -- Security techniques -- Encryption algorithms -- Part 3: Block ciphers. ISO. December 2010. 2017-09-05.
    15. Web site: NIST Special Publication 800-57: Recommendation for Key Management Part 1: General. https://web.archive.org/web/20160207114509/http://nvlpubs.nist.gov/nistpubs/SpecialPublications/NIST.SP.800-57pt1r4.pdf . 2016-02-07 . live. Elaine. Barker. 4. January 2016. NIST. 2017-09-05.
    16. Web site: The Cryptography Guide: Triple DES. Cryptography World. https://web.archive.org/web/20170312125442/http://www.cryptographyworld.com/des.htm. 2017-03-12. dead. 2017-09-05.
    17. Book: Introduction to Modern Cryptography. Jonathan. Katz. Yehuda. Lindell. 2015. Chapman and Hall/CRC. 223. 9781466570269.
    18. http://csrc.nist.gov/publications/nistpubs/800-38a/sp800-38a.pdf NIST Special Publication 800-38A, Recommendation for Block Cipher Modes of Operation, Methods and Techniques, 2001 Edition
    19. Web site: ISO/IEC 10116:2006 Information technology -- Security techniques -- Modes of operation for an n-bit block cipher. 3. February 2006. 2017-09-05.
    20. Ralph Merkle . Ralph . Merkle . Martin Hellman . Martin . Hellman . On the Security of Multiple Encryption . . 24 . 7 . 465–467 . July 1981 . 10.1145/358699.358718 . 10.1.1.164.251 . 11583508 . 2013-11-15 . 2013-02-10 . https://web.archive.org/web/20130210011347/http://cs.jhu.edu/~sdoshi/crypto/papers/p465-merkle.pdf . dead .
    21. Paul van Oorschot . Paul . van Oorschot . Michael J. Wiener . Michael J. . Wiener . 10.1.1.66.6575 . A known-plaintext attack on two-key triple encryption . EUROCRYPT'90, LNCS 473 . 1990 . 318–325 .
    22. Web site: Update to Current Use and Deprecation of TDEA . nist.gov . 11 July 2017 . 2 August 2019.
    23. Web site: Sweet32: Birthday attacks on 64-bit block ciphers in TLS and OpenVPN. sweet32.info. 2017-09-05.
    24. Web site: The SWEET32 Issue, CVE-2016-2183. Rich. Salz. 2016-08-24. OpenSSL. 2017-09-05.
    25. Book: EMV 4.2: Book 2 – Security and Key Management. June 2008. EMVCo. 137. Annex B Approved Cryptographic Algorithms – B1.1 Data Encryption Standard (DES). http://www.emvco.com/specifications.aspx?id=155. 4.2. The double-length key triple DES encipherment algorithm (see ISO/IEC 18033-3) is the approved cryptographic algorithm to be used in the encipherment and MAC mechanisms specified in Annex A1. The algorithm is based on the (single) DES algorithm standardised in ISO 16609.. 2009-03-21. 2017-07-18. https://web.archive.org/web/20170718005134/http://emvco.com/specifications.aspx?id=155. dead.
    26. Web site: Escapa . Daniel . 2006-11-09 . Encryption for Password Protected Sections . Daniel Escapa's OneNote Blog . 2010-01-28 . https://web.archive.org/web/20091216150415/http://blogs.msdn.com/descapa/archive/2006/11/09/encryption-for-password-protected-sections.aspx . 2009-12-16 . live.
    27. Web site: Encrypt e-mail messages – Outlook – Microsoft Office Online . Applies to: Microsoft Office Outlook 2007 . office.microsoft.com . https://web.archive.org/web/20081225033340/http://office.microsoft.com/en-us/outlook/HP012305361033.aspx . 2008-12-25 . dead .
    28. Microsoft TechNet product documentation, Technical Reference for Cryptographic Controls Used in Configuration Manager, October 2012.
    29. Web site: Admin Portal . 2023-03-14 . portal.office.com.
    30. https://dxr.mozilla.org/mozilla-central/source/security/nss/lib/pk11wrap/pk11sdr.c#248 Mozilla NSS source code

    This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Triple DES".

    Except where otherwise indicated, Everything.Explained.Today is © Copyright 2009-2024, A B Cryer, All Rights Reserved. Cookie policy.