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Semelhante a "The Sorry State of SSL" Hynek Schlawack, PyConRu 2014
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"The Sorry State of SSL" Hynek Schlawack, PyConRu 2014
- 1. THE SORRY STATE OF ССЛ Hynek Schlawack
- 8. WTF
- 9. WTF SSL
- 10. WTF SSL & TLS
- 11. TIMELINE
- 12. TIMELINE 1995: Secure Sockets Layer 2.0, Netscape
- 13. TIMELINE 1995: Secure Sockets Layer 2.0, Netscape 1996: SSL 3.0, still Netscape
- 14. TIMELINE 1995: Secure Sockets Layer 2.0, Netscape 1996: SSL 3.0, still Netscape 1999: Transport Layer Security 1.0, IETF
- 15. TIMELINE 1995: Secure Sockets Layer 2.0, Netscape 1996: SSL 3.0, still Netscape 1999: Transport Layer Security 1.0, IETF 2006: TLS 1.1
- 16. TIMELINE 1995: Secure Sockets Layer 2.0, Netscape 1996: SSL 3.0, still Netscape 1999: Transport Layer Security 1.0, IETF 2006: TLS 1.1 2008: TLS 1.2
- 17. 2013
- 19. 2013 • newfound scrutiny • browsers add TLS 1.2
- 20. 2013 • newfound scrutiny • browsers add TLS 1.2 • just using TLS not enough
- 21. TLS
- 22. TLS • identity
- 24. TLS • identity • confidentiality • integrity
- 25. TLS HYGIENE
- 26. SERVERS
- 27. BE UP-TO-DATE • OpenSSL >= 1.0.1c • Apache >= 2.4.0 • nginx >= 1.0.6 or 1.1.0
- 28. BE UP-TO-DATE • OpenSSL >= 1.0.1c • Apache >= 2.4.0 • nginx >= 1.0.6 or 1.1.0 g
- 30. CERTIFICATES • identity • validity • CA sig
- 31. CERTIFICATES • identity • validity • CA sig
- 32. CERTIFICATES • identity • validity • CA sig
- 33. CERTIFICATES • identity • validity • CA sig
- 34. CERTIFICATES • identity • validity • CA sig
- 37. TRUST CHAIN
- 38. TRUST CHAIN
- 39. TRUST CHAIN
- 41. CERTIFICATES • trust chain • host name/service
- 42. CERTIFICATES • trust chain • host name/service • already/still valid?
- 44. DISABLE • SSL 2.0 • SSL 3.0 (if you can)
- 45. DISABLE • SSL 2.0 • SSL 3.0 (if you can) • TLS compression
- 46. CIPHER SUITES
- 47. CIPHER
- 48. CIPHER Cipher
- 53. CIPHER: MODE
- 55. CIPHER: MODE • CBC • stream ciphers
- 56. CIPHER: MODE • CBC • stream ciphers • GCM
- 60. ENCRYPTION: FALL BACK TO AES128-CBC
- 61. ENCRYPTION: IF LIFE IS CRUEL TO YOU 3DES-CBC
- 62. ENCRYPTION: EOL
- 64. ENCRYPTION: DANGEROUS • EXP-* • DES
- 65. ENCRYPTION: DANGEROUS • EXP-* • DES • RC4
- 66. ENCRYPTION: DANGEROUS • EXP-* • DES • RC4
- 67. KEY EXCHANGE
- 68. KEY EXCHANGE fast PFS RSA ✔️ ❌
- 69. KEY EXCHANGE fast PFS RSA ✔️ ❌ DHE ❌ ✔️
- 70. KEY EXCHANGE fast PFS RSA ✔️ ❌ DHE ❌ ✔️ ECDHE ✔️ ✔️
- 71. KEY EXCHANGE fast PFS RSA ✔️ ❌ DHE ❌ ✔️ ECDHE ✔️ ✔️
- 72. INTEGRITY: MACS • Message Authentication Code
- 73. INTEGRITY: MACS • Message Authentication Code • HMAC
- 74. INTEGRITY: MACS • Message Authentication Code • HMAC • GCM
- 75. HAVE THE LAST WORD
- 76. YOU’RE DONE!
- 77. YOU’RE DONE! (but test your results!)
- 78. CERTIFICATE
- 79. CERTIFICATE
- 80. CERTIFICATE
- 81. CERTIFICATE
- 82. CERTIFICATE
- 83. CERTIFICATE
- 84. CERTIFICATE
- 85. PROTOCOLS
- 86. PROTOCOLS
- 87. PROTOCOLS
- 88. PROTOCOLS
- 89. CIPHER SUITES
- 90. CIPHER SUITES
- 91. CIPHER SUITES
- 92. CIPHER SUITES
- 93. CIPHER SUITES
- 94. CIPHER SUITES
- 95. CIPHER SUITES
- 96. CIPHER SUITES
- 97. CLIENTS
- 98. YOU HAD ONE JOB!
- 99. YOU HAD ONE JOB! VERIFY!
- 100. VERIFY THE CERTIFICATE! • valid?
- 101. VERIFY THE CERTIFICATE! • valid? • trustworthy chain?
- 102. VERIFY THE CERTIFICATE! • valid? • trustworthy chain? • correct hostname/service?
- 103. TRUST CHAIN
- 105. TRUST CHAIN • VERIFY_PEER • trust stores OS dependent
- 106. TRUST CHAIN • VERIFY_PEER • trust stores OS dependent • SSL_CTX_set_default_ verify_paths
- 107. SYSTEM CA • FreeBSD: ca_root_nss
- 108. SYSTEM CA • FreeBSD: ca_root_nss • debian/Red Hat: ca-certificates
- 109. SYSTEM CA • FreeBSD: ca_root_nss • debian/Red Hat: ca-certificates • OS X: TEA or homebrew
- 110. SYSTEM CA • FreeBSD: ca_root_nss • debian/Red Hat: ca-certificates • OS X: TEA or homebrew • Windows: wincertstore
- 111. SYSTEM CA • FreeBSD: ca_root_nss • debian/Red Hat: ca-certificates • OS X: TEA or homebrew • Windows: wincertstore • or: Mozilla/certifi
- 112. HOSTNAME VERIFICATION OpenSSL to developers:
- 113. HOSTNAME VERIFICATION OpenSSL to developers: LOL
- 114. DON’T VERIFY TRUST CHAIN I can pretend to be Google with any self-signed certificate.
- 115. DON’T VERIFY HOSTNAME I can pretend to be Google with any valid certificate.
- 117. SET SOME OPTIONS • acceptable ciphers • disable SSL 2.0
- 118. THAT’S ALL!
- 119. USERS
- 121. FUNDAMENTAL MISCONCEPTIONS • no end-to-end security
- 122. FUNDAMENTAL MISCONCEPTIONS • no end-to-end security • metadata
- 123. VPN?
- 124. VPN? • sees all your traffic
- 125. VPN? • sees all your traffic • same for CDN
- 129. TRUST ISSUES
- 130. TRUST ISSUES
- 131. TRUST ISSUES
- 132. TRUST ISSUES
- 134. TRUST ISSUES • hacked • screw up
- 135. TRUST ISSUES • hacked • screw up • court orders
- 136. TRUST ISSUES • hacked • screw up • court orders • big corp
- 138. DON’T DO IT YOURSELF IF YOU CAN HELP IT. Rule of Thumb
- 140. STANDARD LIBRARY
- 141. STANDARD LIBRARY • terrible pre-3.3
- 142. STANDARD LIBRARY • terrible pre-3.3 • very incomplete in 2.7
- 143. STANDARD LIBRARY • terrible pre-3.3 • very incomplete in 2.7 • PFS impossible
- 144. STANDARD LIBRARY • terrible pre-3.3 • very incomplete in 2.7 • PFS impossible • missing options
- 145. STANDARD LIBRARY • terrible pre-3.3 • very incomplete in 2.7 • PFS impossible • missing options • bound to Python’s OpenSSL
- 146. HOSTNAME VERIFICATION 3.2– from ssl import match_hostname 2.4–2.7 pip install backports.ssl_match_hostname
- 147. PYOPENSSL
- 148. PYOPENSSL • Python 2.6+, 3.2+, and PyPy
- 149. PYOPENSSL • Python 2.6+, 3.2+, and PyPy • more complete API coverage
- 150. PYOPENSSL • Python 2.6+, 3.2+, and PyPy • more complete API coverage • PyCA cryptography!
- 151. CRYPTOGRAPHY.IO
- 152. CRYPTOGRAPHY.IO • Python crypto w/o footguns
- 153. CRYPTOGRAPHY.IO • Python crypto w/o footguns • PyCA
- 154. CRYPTOGRAPHY.IO • Python crypto w/o footguns • PyCA • PyPy ♥ CFFI
- 155. CRYPTOGRAPHY.IO • Python crypto w/o footguns • PyCA • PyPy ♥ CFFI • gives pyOpenSSL momentum
- 158. SERVERS lib PFS good defaults configurable eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ gunicorn depends ❌ ❌ ❌ Tornado stdlib ❌ ❌ ❌
- 159. SERVERS lib PFS good defaults configurable eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ gunicorn depends ❌ ❌ ❌ Tornado stdlib ❌ ❌ ❌ Twisted 14.0 pyOpenSSL ✔️ ✔️ ✔️
- 160. SERVERS lib PFS good defaults configurable eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ gunicorn depends ❌ ❌ ❌ Tornado stdlib ❌ ❌ ❌ Twisted 14.0 pyOpenSSL ✔️ ✔️ ✔️ uWSGI own C code ✔️ ❌ ✔️
- 161. SERVERS lib PFS good defaults configurable eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ gunicorn depends ❌ ❌ ❌ Tornado stdlib ❌ ❌ ❌ Twisted 14.0 pyOpenSSL ✔️ ✔️ ✔️ uWSGI own C code ✔️ ❌ ✔️
- 162. CLIENTS lib verifies certificates verifies hostnames good defaults eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌
- 163. CLIENTS lib verifies certificates verifies hostnames good defaults eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ Tornado stdlib ✔️ ✔️ ❌
- 164. CLIENTS lib verifies certificates verifies hostnames good defaults eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ Tornado stdlib ✔️ ✔️ ❌ Twisted 14.0 pyOpenSSL depends depends ✔️
- 165. CLIENTS lib verifies certificates verifies hostnames good defaults eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ Tornado stdlib ✔️ ✔️ ❌ Twisted 14.0 pyOpenSSL depends depends ✔️ urllib2 stdlib ❌ ❌ ❌
- 166. CLIENTS lib verifies certificates verifies hostnames good defaults eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ Tornado stdlib ✔️ ✔️ ❌ Twisted 14.0 pyOpenSSL depends depends ✔️ urllib2 stdlib ❌ ❌ ❌ urllib3/requests hybrid ✔️ ✔️ ✔️
- 167. SUMMARY
- 168. SUMMARY • keep TLS out of Python if you can
- 169. SUMMARY • keep TLS out of Python if you can • use pyOpenSSL-powered requests for HTTPS
- 170. SUMMARY • keep TLS out of Python if you can • use pyOpenSSL-powered requests for HTTPS • write servers in Twisted
- 171. SUMMARY • keep TLS out of Python if you can • use pyOpenSSL-powered requests for HTTPS • write servers in Twisted • use pyOpenSSL
- 172. SUMMARY • keep TLS out of Python if you can • use pyOpenSSL-powered requests for HTTPS • write servers in Twisted • use pyOpenSSL • use Python 2 stdlib only for clients
- 173. WHY SORRY?
- 174. IMPLEMENTATIONS
- 175. IMPLEMENTATIONS
- 176. USERS
- 177. USERS • run outdated software
- 178. USERS • run outdated software • click certificate warnings away
- 179. USERS • run outdated software • click certificate warnings away • are at the mercy of 3rd parties
- 180. SERVERS
- 181. SERVERS
- 182. CLIENTS
- 183. PYTHON Is at the forefront of terrible.
- 184. HOPE
- 185. HOPE • people care again
- 186. HOPE • people care again • stdlib
- 187. HOPE • people care again • stdlib • PyCA
- 188. CALLS TO ACTION
- 189. CALLS TO ACTION
- 190. CALLS TO ACTION
- 191. CALLS TO ACTION
- 192. CALLS TO ACTION