The Sorry State of SSL at PyCon US 2014

Those web pages with shiny lock icons boasting that your data is safe because of “256 bit encryption”? They are lying. In times of mass surveillance and commercialized Internet crime you should know why that’s the case. This talk will give you an overview that will help you to assess your personal security more realistically and to make your applications as secure as possible against all odds.

Transcript

1. THE SORRY STATE OF SSL Hynek Schlawack
2. @hynek https://hynek.me https://github.com/hynek https://www.variomedia.de Hi!
6. ONLY LINK ox.cx/t
7. WTF
8. WTF SSL
9. WTF SSL & TLS
10. TIMELINE
11. TIMELINE 1995: Secure Sockets Layer 2.0, Netscape
12. TIMELINE 1995: Secure Sockets Layer 2.0, Netscape 1996: SSL 3.0, still Netscape
13. TIMELINE 1995: Secure Sockets Layer 2.0, Netscape 1996: SSL 3.0, still Netscape 1999: Transport Layer Security 1.0, IETF
14. 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
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 2008: TLS 1.2
17. 2013 • newfound scrutiny
18. 2013 • newfound scrutiny • browsers add TLS 1.2
19. 2013 • newfound scrutiny • browsers add TLS 1.2 • just using TLS not enough
20. TLS
21. TLS • identity
22. TLS • identity • confidentiality
23. TLS • identity • confidentiality • integrity
24. TLS HYGIENE
25. SERVERS
26. BE UP-TO-DATE • OpenSSL >= 1.0.1c • Apache >= 2.4.0 • nginx >= 1.0.6 or 1.1.0
27. CERTIFICATES • identity • validity
28. CERTIFICATES • identity • validity • CA sig
29. CERTIFICATES • identity • validity • CA sig
30. CERTIFICATES • identity • validity • CA sig
31. CERTIFICATES • identity • validity • CA sig
32. CERTIFICATES • identity • validity • CA sig
33. EXTENDED VALIDATION CERTIFICATES
34. EXTENDED VALIDATION CERTIFICATES
35. TRUST CHAIN
36. TRUST CHAIN
37. TRUST CHAIN
38. CERTIFICATES • trust chain
39. CERTIFICATES • trust chain • host name/service
40. CERTIFICATES • trust chain • host name/service • already/still valid?
41. DISABLE • SSL 2.0
42. DISABLE • SSL 2.0 • SSL 3.0 (if you can)
43. DISABLE • SSL 2.0 • SSL 3.0 (if you can) • TLS compression
44. CIPHER SUITES
45. CIPHER
46. CIPHER Cipher
47. CIPHER Cipher Plaintext
48. CIPHER Cipher Plaintext
49. CIPHER Cipher Ciphertext Plaintext
50. Ciphertext CIPHER Cipher Plaintext
51. CIPHER: MODE
52. CIPHER: MODE • CBC
53. CIPHER: MODE • CBC • stream ciphers
54. CIPHER: MODE • CBC • stream ciphers • GCM
55. ENCRYPTION: PREFER THIS
56. ENCRYPTION: PREFER THIS AES128-GCM &
57. ENCRYPTION: PREFER THIS AES128-GCM & ChaCha20
58. ENCRYPTION: FALL BACK TO AES128-CBC
59. ENCRYPTION: IF LIFE IS CRUEL TO YOU 3DES-CBC
60. ENCRYPTION: EOL
61. ENCRYPTION: DANGEROUS • EXP-*
62. ENCRYPTION: DANGEROUS • EXP-* • DES
63. ENCRYPTION: DANGEROUS • EXP-* • DES • RC4
64. KEY EXCHANGE
65. KEY EXCHANGE fast PFS RSA ✔️ ❌
66. KEY EXCHANGE fast PFS RSA ✔️ ❌ DHE ❌ ✔️
67. KEY EXCHANGE fast PFS RSA ✔️ ❌ DHE ❌ ✔️ ECDHE ✔️ ✔️
68. KEY EXCHANGE fast PFS RSA ✔️ ❌ DHE ❌ ✔️ ECDHE ✔️ ✔️
69. INTEGRITY: MACS • Message Authentication Code
70. INTEGRITY: MACS • Message Authentication Code • HMAC
71. INTEGRITY: MACS • Message Authentication Code • HMAC • GCM
72. HAVE THE LAST WORD
73. YOU’RE DONE!
74. YOU’RE DONE! (but test your results!)
75. CERTIFICATE
76. CERTIFICATE
77. CERTIFICATE
78. CERTIFICATE
79. CERTIFICATE
80. CERTIFICATE
81. CERTIFICATE
82. PROTOCOLS
83. PROTOCOLS
84. PROTOCOLS
85. PROTOCOLS
86. CIPHER SUITES
87. CIPHER SUITES
88. CIPHER SUITES
89. CIPHER SUITES
90. CIPHER SUITES
91. CIPHER SUITES
92. CIPHER SUITES
93. CIPHER SUITES
94. CLIENTS
95. YOU HAD ONE JOB!
96. YOU HAD ONE JOB! VERIFY!
97. VERIFY THE CERTIFICATE! • valid?
98. VERIFY THE CERTIFICATE! • valid? • trustworthy chain?
99. VERIFY THE CERTIFICATE! • valid? • trustworthy chain? • correct hostname/service?
100. TRUST CHAIN
101. TRUST CHAIN • VERIFY_PEER
102. TRUST CHAIN • VERIFY_PEER • trust stores OS dependent
103. TRUST CHAIN • VERIFY_PEER • trust stores OS dependent • SSL_CTX_set_default_ verify_paths
104. SYSTEM CA • FreeBSD: ca_root_nss
105. SYSTEM CA • FreeBSD: ca_root_nss • debian/Red Hat: ca-certificates
106. SYSTEM CA • FreeBSD: ca_root_nss • debian/Red Hat: ca-certificates • OS X: TEA or homebrew
107. SYSTEM CA • FreeBSD: ca_root_nss • debian/Red Hat: ca-certificates • OS X: TEA or homebrew • Windows: wincertstore
108. SYSTEM CA • FreeBSD: ca_root_nss • debian/Red Hat: ca-certificates • OS X: TEA or homebrew • Windows: wincertstore • or: Mozilla/certifi
109. HOSTNAME VERIFICATION OpenSSL to developers:
110. HOSTNAME VERIFICATION OpenSSL to developers: LOL
111. DON’T VERIFY TRUST CHAIN I can pretend to be Google with any self-signed certificate.
112. DON’T VERIFY HOSTNAME I can pretend to be Google with any valid certificate.
114. SET SOME OPTIONS • acceptable ciphers • disable SSL 2.0
115. THAT’S ALL!
116. USERS
117. FUNDAMENTAL MISCONCEPTIONS
118. FUNDAMENTAL MISCONCEPTIONS • no end-to-end security
119. FUNDAMENTAL MISCONCEPTIONS • no end-to-end security • metadata
120. VPN?
121. VPN? • sees all your traffic
122. VPN? • sees all your traffic • same for CDN
123. CERTIFICATE WARNINIGS
124. CERTIFICATE WARNINIGS
125. ROOT CERTIFICATE POISONING
126. TRUST ISSUES
127. TRUST ISSUES
128. TRUST ISSUES
129. TRUST ISSUES
130. TRUST ISSUES • hacked
131. TRUST ISSUES • hacked • screw up
132. TRUST ISSUES • hacked • screw up • court orders
133. TRUST ISSUES • hacked • screw up • court orders • big corp
135. DON’T DO IT YOURSELF IF YOU CAN HELP IT. Rule of Thumb
136. STANDARD LIBRARY VS. PYOPENSSL
137. STANDARD LIBRARY
138. STANDARD LIBRARY • terrible pre-3.3
139. STANDARD LIBRARY • terrible pre-3.3 • very incomplete in 2.7
140. STANDARD LIBRARY • terrible pre-3.3 • very incomplete in 2.7 • PFS impossible
141. STANDARD LIBRARY • terrible pre-3.3 • very incomplete in 2.7 • PFS impossible • missing options
142. STANDARD LIBRARY • terrible pre-3.3 • very incomplete in 2.7 • PFS impossible • missing options • bound to Python’s OpenSSL
143. HOSTNAME VERIFICATION 3.2– from ssl import match_hostname 2.4–2.7 pip install backports.ssl_match_hostname
144. PYOPENSSL
145. PYOPENSSL • Python 2.6+, 3.2+, and PyPy
146. PYOPENSSL • Python 2.6+, 3.2+, and PyPy • more complete API coverage
147. PYOPENSSL • Python 2.6+, 3.2+, and PyPy • more complete API coverage • no server ECDHE (yet)
148. PYOPENSSL • Python 2.6+, 3.2+, and PyPy • more complete API coverage • no server ECDHE (yet) • cryptography!
149. CRYPTOGRAPHY.IO
150. CRYPTOGRAPHY.IO • Python crypto w/o footguns
151. CRYPTOGRAPHY.IO • Python crypto w/o footguns • PyPy ♥ cffi
152. CRYPTOGRAPHY.IO • Python crypto w/o footguns • PyPy ♥ cffi • SecureTransport is coming!
153. CRYPTOGRAPHY.IO • Python crypto w/o footguns • PyPy ♥ cffi • SecureTransport is coming! • gives pyOpenSSL momentum
154. HOSTNAME VERIFICATION service_identity
155. LIBRARIES & FRAMEWORKS
156. SERVERS lib PFS good defaults configurable eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ gunicorn depends ❌ ❌ ❌ Tornado stdlib ❌ ❌ ❌
157. SERVERS lib PFS good defaults configurable eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ gunicorn depends ❌ ❌ ❌ Tornado stdlib ❌ ❌ ❌ Twisted 14.0 pyOpenSSL ✔️ ✔️ ✔️
158. SERVERS lib PFS good defaults configurable eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ gunicorn depends ❌ ❌ ❌ Tornado stdlib ❌ ❌ ❌ Twisted 14.0 pyOpenSSL ✔️ ✔️ ✔️ uWSGI own C code ✔️ ❌ ✔️
159. SERVERS lib PFS good defaults configurable eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ gunicorn depends ❌ ❌ ❌ Tornado stdlib ❌ ❌ ❌ Twisted 14.0 pyOpenSSL ✔️ ✔️ ✔️ uWSGI own C code ✔️ ❌ ✔️
160. CLIENTS lib verifies certificates verifies hostnames good defaults eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌
161. CLIENTS lib verifies certificates verifies hostnames good defaults eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ Tornado stdlib ✔️ ✔️ ❌
162. CLIENTS lib verifies certificates verifies hostnames good defaults eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ Tornado stdlib ✔️ ✔️ ❌ Twisted 14.0 pyOpenSSL opt-in opt-in ✔️
163. CLIENTS lib verifies certificates verifies hostnames good defaults eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ Tornado stdlib ✔️ ✔️ ❌ Twisted 14.0 pyOpenSSL opt-in opt-in ✔️ urllib2 stdlib ❌ ❌ ❌
164. CLIENTS lib verifies certificates verifies hostnames good defaults eventlet hybrid ❌ ❌ ❌ gevent stdlib ❌ ❌ ❌ Tornado stdlib ✔️ ✔️ ❌ Twisted 14.0 pyOpenSSL opt-in opt-in ✔️ urllib2 stdlib ❌ ❌ ❌ urllib3/requests hybrid ✔️ ✔️ ✔️
165. SUMMARY
166. SUMMARY • keep TLS out of Python if you can
167. SUMMARY • keep TLS out of Python if you can • use pyOpenSSL-powered requests for HTTPS
168. SUMMARY • keep TLS out of Python if you can • use pyOpenSSL-powered requests for HTTPS • write servers in Twisted
169. SUMMARY • keep TLS out of Python if you can • use pyOpenSSL-powered requests for HTTPS • write servers in Twisted • use pyOpenSSL
170. 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
171. WHY SORRY?
172. IMPLEMENTATIONS
173. IMPLEMENTATIONS
174. USERS
175. USERS • run outdated software
176. USERS • run outdated software • click certificate warnings away
177. USERS • run outdated software • click certificate warnings away • are at the mercy of 3rd parties
178. SERVERS
179. SERVERS
180. CLIENTS
181. CLIENTS
182. PYTHON Is at the forefront of terrible.
183. HOPE
184. HOPE • people care again
185. HOPE • people care again • stdlib
186. HOPE • people care again • stdlib • PyCA
187. CALLS TO ACTION
188. CALLS TO ACTION
189. CALLS TO ACTION
190. CALLS TO ACTION
191. CALLS TO ACTION
192. ox.cx/t @hynek Crypto Open Space!