Cryptography Pitfalls at CactusCon 2019

Transcript

1. Cryptography Pitfalls
   John Downey | @jtdowney
   @jtdowney 1
   

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2. @jtdowney 2
   

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3. The views expressed in this
   presentation are my own, and not
   those of PayPal or any of its
   affiliates.
   @jtdowney 3
   

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4. @jtdowney 4
   

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5. Confidentiality
   @jtdowney 5
   

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6. Authentication
   @jtdowney 6
   

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7. Identification
   @jtdowney 7
   

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8. Rigorous Science
   @jtdowney 8
   

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9. Peer Review
   @jtdowney 9
   

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10. @jtdowney 10
    

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11. You have probably seen the door to a bank vault, at least in
    the movies. You know, 10-inch-thick, hardened steel, with huge
    bolts to lock it in place. It certainly looks impressive. We
    often find the digital equivalent of such a vault door installed
    in a tent. The people standing around it are arguing over how
    thick the door should be, rather than spending their time
    looking at the tent.
    — Cryptography Engineering by Niels Ferguson, Bruce
    Schneier, and Tadayoshi Kohno
    @jtdowney 11
    

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12. • For data in transit
    • Use TLS, SSH, or VPN/IPsec
    • For data at rest
    • Use GnuPG
    • Data to be signed
    • Use GnuPG
    @jtdowney 12
    

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13. • Avoid low level libraries
    • OpenSSL
    • PyCrypto
    • Bouncy Castle
    • Use a high level library
    • NaCL/libsodium (C, Ruby, PHP, etc)
    • Keyczar (C++, Python, and Java)
    @jtdowney 13
    

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14. @jtdowney 14
    

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15. Random Number
    Generation
    @jtdowney 15
    

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16. Pitfalls
    1. Not using a cryptographically strong random number
    generator
    2. Not using random data when it is required
    3. Broken random number generators
    @jtdowney 16
    

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17. @jtdowney 17
    

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18. @jtdowney 18
    

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19. Pitfalls
    1. Not using a cryptographically strong random number
    generator
    2. Not using random data when it is required
    3. Broken random number generators
    @jtdowney 19
    

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20. @jtdowney 20
    

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21. Pitfalls
    1. Not using a cryptographically strong random number
    generator
    2. Not using random data when it is required
    3. Broken random number generators
    @jtdowney 21
    

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22. @jtdowney 22
    

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23. @jtdowney 23
    

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24. @jtdowney 24
    

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26. MD_Update(&m,buf,j);
    @jtdowney 26
    

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27. Don't add uninitialised data to
    the random number generator.
    This stop valgrind from giving
    error messages in unrelated code.
    (Closes: #363516)
    @jtdowney 27
    

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28. /* DO NOT REMOVE THE FOLLOWING CALL TO MD_Update()! */
    MD_Update(&m,buf,j);
    /* We know that line may cause programs such as
    purify and valgrind to complain about use of
    uninitialized data. The problem is not, it's
    with the caller. Removing that line will make
    sure you get really bad randomness and thereby
    other problems such as very insecure keys. */
    @jtdowney 28
    

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29. Recommendations
    • Use a cryptographically strong random number generator
    • Unix-like
    • Read from /dev/urandom
    • Windows
    • RandomNumberGenerator in System.Security.Cryptography (.NET)
    • CryptGenRandom
    • Java use java.security.SecureRandom
    @jtdowney 29
    

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30. Hash Functions
    @jtdowney 30
    

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31. Pitfalls
    1. Using weak/old algorithms
    2. Misunderstanding checksums
    3. Length extension attacks
    @jtdowney 31
    

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32. @jtdowney 32
    

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33. @jtdowney 33
    

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34. @jtdowney 34
    

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35. @jtdowney 35
    

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36. 9EC4C12949A4F31474F299058CE2B22A
    @jtdowney 36
    

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37. 9EC4C12949A4F31474F299058CE2B22A
    USCYBERCOM plans, coordinates, integrates, synchronizes
    and conducts activities to: direct the operations and defense of
    specified Department of Defense information networks and;
    prepare to, and when directed, conduct full spectrum military
    cyberspace operations in order to enable actions in all
    domains, ensure US/Allied freedom of action in cyberspace
    and deny the same to our adversaries.
    @jtdowney 37
    

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38. Pitfalls
    1. Using weak/old algorithms
    2. Misunderstanding checksums
    3. Length extension attacks
    @jtdowney 38
    

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39. @jtdowney 39
    

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40. Pitfalls
    1. Using weak/old algorithms
    2. Misunderstanding checksums
    3. Length extension attacks
    @jtdowney 40
    

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41. Message Authentication Code (MAC)
    tag = MAC(key, value)
    • Takes:
    • key - shared secret
    • value - value to protected integrity of
    • Returns:
    • tag - value that represents the integrity
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42. Naive approach
    tag = sha256(key + value)
    @jtdowney 42
    

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43. Length Extension Attacks
    secret = "my-secret-key"
    value = "buy 10 units at $1"
    signature = sha256(secret + value)
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44. Length Extension Attacks
    secret = "my-secret-key"
    value = "buy 10 units at $1" + " or $0"
    signature = sha256(secret + value)
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45. Fixed
    secret = "my-secret-key"
    value = "buy 10 units at $1"
    signature = hmac_sha256(secret, value)
    @jtdowney 45
    

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46. @jtdowney 46
    

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47. @jtdowney 47
    

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48. Recommendations
    • Use SHA-256 (SHA-2 family)
    • Choose HMAC-SHA-256 if you want a signature
    • Use BLAKE2b if you need speed
    • Stop using MD5
    • Stop using SHA1
    @jtdowney 48
    

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49. Ciphers
    @jtdowney 49
    

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50. Pitfalls
    1. Using old/weak algorithms
    2. Using ECB mode for block ciphers
    3. Not using authenticated encryption
    @jtdowney 50
    

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51. @jtdowney 51
    

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52. @jtdowney 52
    

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53. @jtdowney 53
    

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54. Pitfalls
    1. Using old/weak algorithms
    2. Using ECB mode for block ciphers
    3. Not using authenticated encryption
    @jtdowney 54
    

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55. AES - primitive
    ciphertext = AES_Encrypt(key, plaintext)
    plaintext = AES_Decrypt(key, ciphertext)
    • Function over:
    • key - 128, 192, or 256 bit value
    • plaintext - 128 bit value
    • ciphertext - 128 bit value
    @jtdowney 55
    

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56. ECB Encrypt
    while (remaining blocks) {
    block = ... # next 16 byte (128 bit chunk)
    ouput.append(AES_Encrypt(key, block))
    }
    @jtdowney 56
    

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57. @jtdowney 57
    

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58. @jtdowney 58
    

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59. Pitfalls
    1. Using old/weak algorithms
    2. Using ECB mode for block ciphers
    3. Not using authenticated encryption
    @jtdowney 59
    

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60. @jtdowney 60
    

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61. @jtdowney 61
    

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62. @jtdowney 62
    

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63. @jtdowney 63
    

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64. World of hurt
    @jtdowney 64
    

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65. Recommendations
    • Prefer to use box/secret box from NaCL/libsodium
    • Stop using DES
    • Stop building your own on top of AES
    • Stop encrypting without protecting integrity
    @jtdowney 65
    

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66. What if you have to use AES
    • Do not use ECB mode
    • Be sure to use authenticated encryption
    • GCM mode would be a good first choice
    • Verify the tag/MAC first
    • Still easy to mess up in a critical way
    @jtdowney 66
    

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67. TLS/SSL
    @jtdowney 67
    

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68. Pitfalls
    1. Not verifying the certificate chain or hostname
    2. Misconfigured server settings
    3. Using a broken library
    4. Shipping your private key
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69. @jtdowney 69
    

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70. @jtdowney 70
    

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71. @jtdowney 71
    

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72. @jtdowney 72
    

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73. Hostname verification
    @jtdowney 73
    

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74. Hostname verification
    • Check that you got the certificate for who you intended to
    connect to
    • Hostname verification is protocol dependent
    • OpenSSL doesn't have it built in
    @jtdowney 74
    

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75. Pitfalls
    1. Not verifying the certificate chain or hostname
    2. Misconfigured server settings
    3. Using a broken library
    4. Shipping your private key
    @jtdowney 75
    

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76. @jtdowney 76
    

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77. SSL Labs
    https://www.ssllabs.com
    @jtdowney 77
    

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78. testssl.sh
    https://testssl.sh
    @jtdowney 78
    

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79. TLS Server Settings
    https://mozilla.github.io/server-side-tls/ssl-config-generator/
    @jtdowney 79
    

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80. Pitfalls
    1. Not verifying the certificate chain or hostname
    2. Misconfigured server settings
    3. Using a broken library
    4. Shipping your private key
    @jtdowney 80
    

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81. @jtdowney 81
    

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82. @jtdowney 82
    

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83. Recommendations
    • Do ensure you're validating connections
    • Lean on a framework/library if possible
    • But check that it also does the right thing
    • Setup and automated test to validate this setting
    (badssl.com)
    @jtdowney 83
    

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84. Pitfalls
    1. Not verifying the certificate chain or hostname
    2. Misconfigured server settings
    3. Using a broken library
    4. Shipping your private key
    @jtdowney 84
    

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85. @jtdowney 85
    

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86. Trust
    @jtdowney 86
    

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87. The authenticity of host 'apollo.local (10.0.2.56)' can't be established.
    RSA key fingerprint is 04:63:c1:ba:c7:31:04:12:14:ff:b6:c4:32:cf:44:ec.
    Are you sure you want to continue connecting (yes/no)?
    @jtdowney 87
    

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88. @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@
    @ WARNING: REMOTE HOST IDENTIFICATION HAS CHANGED! @
    @@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@
    IT IS POSSIBLE THAT SOMEONE IS DOING SOMETHING NASTY!
    Someone could be eavesdropping on you right now (man-in-the-middle attack)!
    It is also possible that the RSA host key has just been changed.
    The fingerprint for the RSA key sent by the remote host is
    04:63:c1:ba:c7:31:04:12:14:ff:b6:c4:32:cf:44:ec.
    Please contact your system administrator.
    @jtdowney 88
    

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89. @jtdowney 89
    

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90. Certificate Pinning
    @jtdowney 90
    

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91. @jtdowney 91
    

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92. Recommendations
    • Think about what organizations you really trust
    • Investigate certificate pinning for your apps
    @jtdowney 92
    

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93. @jtdowney 93
    

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94. Stanford Crypto Class
    http://crypto-class.com
    @jtdowney 94
    

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95. Matasano Crypto Challenges
    http://cryptopals.com
    @jtdowney 95
    

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96. Questions
    John Downey | @jtdowney
    @jtdowney 96
    

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97. Bonus Round
    @jtdowney 97
    

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98. Quantum Computers
    @jtdowney 98
    

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99. Pitfalls
    1. Assuming current crypto will last forever
    @jtdowney 99
    

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100. @jtdowney 100
     

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101. @jtdowney 101
     

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102. Recommendations
     • Follow the PQCrypto discussion
     • Stay away from PQCrypto until the industry starts to
     standardize
     • Hope that researchers are moving fast enough
     @jtdowney 102
     

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103. Images
     • https://flic.kr/p/6eagaw
     • https://flic.kr/p/4KWhKn
     • https://flic.kr/p/9F2BCv
     • https://flic.kr/p/486xYS
     • https://flic.kr/p/7Ffppm
     • https://flic.kr/p/8TuJD9
     • https://flic.kr/p/4iLJZt
     • https://flic.kr/p/4pGZuz
     • https://flic.kr/p/48w7wP
     • https://flic.kr/p/8aZWNE
     • https://flic.kr/p/5NRHp
     • https://flic.kr/p/7p7raq
     • https://flic.kr/p/aZEE1Z
     • https://flic.kr/p/7WtwAz
     • https://flic.kr/p/6AN9mM
     • https://flic.kr/p/6dt62u
     • https://flic.kr/p/4ZqwyB
     • https://flic.kr/p/Bqewr
     • https://flic.kr/p/ecdhVE
     • https://flic.kr/p/AV1Nd
     • https://flic.kr/p/5tWgh4
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