HTTPS is Coming: Are you Prepared?

Google, Firefox, and the IETF are currently engaged in significant initiatives to convert the Web to be secure by default. Page ranking, exciting new browser APIs, and HTTP/2 are all pushing websites to require HTTPS. An HTTPS-only web is imminent. Do you know how to configure HTTPS properly? According to SSL Pulse, 75% of the top 1 million websites that use HTTPS are not actually secure because of misconfiguration. In my talk, I will discuss the key aspects of HTTPS to empower developers to deploy truly secure HTTPS sites.

1. HTTPS is Coming Zack Tollman @tollmanz
3. “Pervasive monitoring is a technical attack that should be mitigated in the design of IETF protocols, where possible.” — IETF https://tools.ietf.org/html/rfc7258
4. “Today we are announcing our intent to phase out non-secure HTTP” — Richard Barnes, Firefox Security Lead https://blog.mozilla.org/security/2015/04/30/deprecating-non-secure-http/
5. HTTP/2 is TLS only in Chrome, Firefox, Opera, IE/Edge, and Safari https://wiki.mozilla.org/Networking/http2
6. Now Later Less TLS More TLS
7. TLS knowledge is now essential
8. We are bad at TLS
9. 68% of sites are not secure https://www.trustworthyinternet.org/ssl-pulse/
10. 95% do not support HSTS https://www.trustworthyinternet.org/ssl-pulse/
11. 25% do not support Perfect Forward Secrecy https://www.trustworthyinternet.org/ssl-pulse/
12. “misconfiguration errors are undermining the potential security” — Kranch & Bonneau (2015) http://www.internetsociety.org/sites/default/files/01_4_0.pdf
13. “industry-wide configuration problem with the deployment of DHE key exchange” — Huang, Adhikarla, Boneh, & Jackson (2014) http://www.w2spconf.com/2014/papers/TLS.pdf
14. We don’t seem to understand TLS
15. Let’s fix that
16. 1. Understand TLS 2. Acquire certificate 3. Configure TLS
17. Quick Note on TLS and SSL
18. SSL v2 SSL v3 TLS v1 TLS v1.1 TLS v1.2 1995 1996 1999 2006 2008
19. Encryption Integrity Authentication Key Exchange
20. Authentication
21. Is the server the intended server?
22. Chain of “trust”
23. End Certificate example.com Signing algorithm Signature Public Key Public Exponent
24. End Intermediate Certificate CA certificate Signature
25. End Root Certificate In browser Signature Intermediate
26. End Intermediate Root Trusts Trusts
27. Integrity
28. Is the message received the message sent?
29. Data Data
30. Data Data Hash Encrypt
31. Data Data Hash Encrypt Encrypt
32. Data Data Hash Encrypt Encrypt Receiver
33. Receiver has encrypted hash and encrypted data
34. E-Hash E-Data
35. E-Hash E-Data P-Hash P-Data
36. E-Hash E-Data P-Hash P-Data Hash
37. Hash Hash =
38. Encryption
39. Converts plaintext to ciphertext
40. c u c j b e y q
41. c u c j b e y q p h p w o r l d
42. A B C D E F N O P Q R S +13
43. Algorithm: Letter + 13 = Cipher Letter
44. Substitution Cipher Caesar Cipher
45. Key
46. Key 13
47. Weak cipher
48. Secrecy in algorithm is a problem
49. Secrecy in key is better
50. Advanced Encryption Standard - Rijndael http://www.moserware.com/2009/09/stick-figure-guide-to-advanced.html
51. Many rounds of substitution and permutations
52. Key Exchange
53. How do we establish an encryption key for 2 unknown parties over an insecure connection?
54. http://en.wikipedia.org/wiki/Enigma_machine#/media/File:Kenngruppenheft.jpg Ben Slivka
55. Couriers delivered the daily keys
56. http://en.wikipedia.org/wiki/Jeff_Bezos#/media/File:Jeff_Bezos%27_iconic_laugh.jpg
57. Doesn’t work for the modern web
58. Diffie-Hellman-Merkle key exchange
59. Each individual has a key by the time the process is complete
60. Demo p = 23 g = 5
61. s is a premaster secret from which the master secret is derived
62. Master secret is the key used for encryption
63. Trapdoor functions
64. Easy one way
65. Impossibly difficult the other way
66. If a, b, g, or p are different, s is different
67. Perfect forward secrecy
68. Lavabit
69. I failed to update the Lavabit SSL configuration to prefer ciphers that provided perfect forward secrecy. — Ladar Levison http://arstechnica.com/security/2013/11/07/op-ed-lavabits-founder-responds-to- cryptographers-criticism/
70. Cipher Suites
71. Combination of algorithms for authentication, integrity, encryption, and key exchange
72. ECDHE-RSA-AES128-GCM-SHA256
73. ECDHE-RSA-AES128-GCM-SHA256 Key Exchange
74. ECDHE-RSA-AES128-GCM-SHA256 Certificate signing algorithm (Authentication)
75. ECDHE-RSA-AES128-GCM-SHA256 Cipher (Encryption)
76. ECDHE-RSA-AES128-GCM-SHA256 Message authentication code (Integrity)
77. ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES128- GCM-SHA256:ECDHE-RSA-AES256-GCM-SHA384:ECDHE- ECDSA-AES256-GCM-SHA384:DHE-RSA-AES128-GCM- SHA256:DHE-DSS-AES128-GCM-SHA256:kEDH +AESGCM:ECDHE-RSA-AES128-SHA256:ECDHE-ECDSA- AES128-SHA256:ECDHE-RSA-AES128-SHA:ECDHE-ECDSA- AES128-SHA:ECDHE-RSA-AES256-SHA384:ECDHE-ECDSA- AES256-SHA384:ECDHE-RSA-AES256-SHA:ECDHE-ECDSA- AES256-SHA:DHE-RSA-AES128-SHA256:DHE-RSA-AES128- SHA:DHE-DSS-AES128-SHA256:DHE-RSA-AES256- SHA256:DHE-DSS-AES256-SHA:DHE-RSA-AES256- SHA:AES128-GCM-SHA256:AES256-GCM-SHA384:AES128- SHA256:AES256-SHA256:AES128-SHA:AES256- SHA:AES:CAMELLIA:DES-CBC3-SHA:!aNULL:!eNULL:! EXPORT:!DES:!RC4:!MD5:!PSK:!aECDH:!EDH-DSS-DES- CBC3-SHA:!EDH-RSA-DES-CBC3-SHA:!KRB5-DES-CBC3- SHA
78. ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES128- GCM-SHA256:ECDHE-RSA-AES256-GCM-SHA384:ECDHE- ECDSA-AES256-GCM-SHA384:DHE-RSA-AES128-GCM- SHA256:DHE-DSS-AES128-GCM-SHA256:kEDH +AESGCM:ECDHE-RSA-AES128-SHA256:ECDHE-ECDSA- AES128-SHA256:ECDHE-RSA-AES128-SHA:ECDHE-ECDSA- AES128-SHA:ECDHE-RSA-AES256-SHA384:ECDHE-ECDSA- AES256-SHA384:ECDHE-RSA-AES256-SHA:ECDHE-ECDSA- AES256-SHA:DHE-RSA-AES128-SHA256:DHE-RSA-AES128- SHA:DHE-DSS-AES128-SHA256:DHE-RSA-AES256- SHA256:DHE-DSS-AES256-SHA:DHE-RSA-AES256- SHA:AES128-GCM-SHA256:AES256-GCM-SHA384:AES128- SHA256:AES256-SHA256:AES128-SHA:AES256- SHA:AES:CAMELLIA:DES-CBC3-SHA:!aNULL:!eNULL:! EXPORT:!DES:!RC4:!MD5:!PSK:!aECDH:!EDH-DSS-DES- CBC3-SHA:!EDH-RSA-DES-CBC3-SHA:!KRB5-DES-CBC3- SHA
79. ECDHE-RSA-AES128-GCM-SHA256:ECDHE-ECDSA-AES128- GCM-SHA256:ECDHE-RSA-AES256-GCM-SHA384:ECDHE- ECDSA-AES256-GCM-SHA384:DHE-RSA-AES128-GCM- SHA256:DHE-DSS-AES128-GCM-SHA256:kEDH +AESGCM:ECDHE-RSA-AES128-SHA256:ECDHE-ECDSA- AES128-SHA256:ECDHE-RSA-AES128-SHA:ECDHE-ECDSA- AES128-SHA:ECDHE-RSA-AES256-SHA384:ECDHE-ECDSA- AES256-SHA384:ECDHE-RSA-AES256-SHA:ECDHE-ECDSA- AES256-SHA:DHE-RSA-AES128-SHA256:DHE-RSA-AES128- SHA:DHE-DSS-AES128-SHA256:DHE-RSA-AES256- SHA256:DHE-DSS-AES256-SHA:DHE-RSA-AES256- SHA:AES128-GCM-SHA256:AES256-GCM-SHA384:AES128- SHA256:AES256-SHA256:AES128-SHA:AES256- SHA:AES:CAMELLIA:DES-CBC3-SHA:!aNULL:!eNULL:! EXPORT:!DES:!RC4:!MD5:!PSK:!aECDH:!EDH-DSS-DES- CBC3-SHA:!EDH-RSA-DES-CBC3-SHA:!KRB5-DES-CBC3- SHA
82. TLS Handshake
83. Client Server ClientHello ServerHello Certificate ServerHelloDone ClientKeyExchange ChangeCipherSpec Finished ChangeCipherSpec Finished Application Data
84. 1. Client hello Cipher suites TLS version Random bytes Client -> Server
85. 2. Server hello Cipher suite choice TLS version choice Server -> Client
86. 3. Certificate Certificate chain sent Cert signature matches auth algorithm Server -> Client
87. 4. Server Key Exchange Info for key exchange Server -> Client
88. 5. Server Hello Done Server has sent all info Server -> Client
89. 6. Client Key Exchange Info for key exchange Client -> Server
90. 7. Change Cipher Spec Enough info for encryption Switch to encryption Client -> Server
91. 8. Finished Signals that handshake is done Client -> Server
92. 9. Change Cipher Spec Server -> Client
93. 10. Finished Server -> Client
94. TLS Handshake demo with Wireshark
95. HTTP Strict Transport Security
96. SSL Stripping http://www.thoughtcrime.org/software/sslstrip/
97. What if HTTP variant was never accessed?
98. HSTS blocks browser from HTTP version of site
99. Set HSTS only after mixed content issues are resolved
100. add_header Strict-Transport- Security 'max-age=31536000';
101. add_header Strict-Transport- Security 'max-age=31536000; includeSubDomains';
102. Mixed Content
103. HTTP assets in HTTPS page is an attack vector
104. Content Security Policy
105. Content-Security-Policy: default-src 'self' https:; font-src https:// fonts.gstatic.com; img-src 'self' https:; style-src ‘self' https: https://fonts.googleapis.com; script-src 'self' https: https://ssl.google-analytics.com
106. Content-Security-Policy: default-src 'self' https:; font-src https:// fonts.gstatic.com; img-src 'self' https:; style-src ‘self' https: https://fonts.googleapis.com; script-src 'self' https: https://ssl.google-analytics.com
107. Content-Security-Policy: default-src 'self' https:; font-src https:// fonts.gstatic.com; img-src 'self' https:; style-src ‘self' https: https://fonts.googleapis.com; script-src 'self' https: https://ssl.google-analytics.com
108. Content-Security-Policy: default-src 'self' https:; font-src https:// fonts.gstatic.com; img-src 'self' https:; style-src ‘self' https: https://fonts.googleapis.com; script-src 'self' https: https://ssl.google-analytics.com
109. Content-Security-Policy: default-src 'self' https:; font-src https:// fonts.gstatic.com; img-src 'self' https:; style-src ‘self' https: https://fonts.googleapis.com; script-src 'self' https: https://ssl.google-analytics.com
110. Content-Security-Policy: default-src 'self' https:; font-src https:// fonts.gstatic.com; img-src 'self' https:; style-src ‘self' https: https://fonts.googleapis.com; script-src 'self' https: https://ssl.google-analytics.com
111. Content-Security-Policy-Report- Only: default-src 'self' https:; font-src https:// fonts.gstatic.com; img-src 'self' https:; style-src ‘self' https: https://fonts.googleapis.com; script-src 'self' https: https://ssl.google-analytics.com; report-uri /beacon.php
112. upgrade-insecure-requests coming soon http://www.w3.org/TR/upgrade-insecure-requests/
113. Automated Certificate Management Environment (ACME)
114. Let’s Encrypt
115. TLS Configuration Needs Maintenance
116. A theoretical weakness became practical. — Ladar Levison http://arstechnica.com/security/2013/11/07/op-ed-lavabits-founder-responds-to- cryptographers-criticism/
117. I missed that development. — Ladar Levison http://arstechnica.com/security/2013/11/07/op-ed-lavabits-founder-responds-to- cryptographers-criticism/