The Razors Edge - Cutting your TLS Baggage
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A talk on effecting change across a large organization, given at O'Reilly Security 2017. Write-up will be posted at https://www.netmeister.org/blog/razors-edge.html
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The Razors Edge - Cutting your TLS Baggage
- 1. @jschaumaO’Reilly Security 2017 Cutting your TLS baggage Jan Schaumann
- 2. A really boring talk. @jschaumaO’Reilly Security 2017
- 3. I really like boring. @jschaumaO’Reilly Security 2017
- 4. I really like boring. I’m so boring, even BoringSSL is too exciting for me. @jschaumaO’Reilly Security 2017
- 7. @jschaumaO’Reilly Security 2017 “There are two types of companies: those that have been hacked and those that don't know it yet.” — every #infosec nerd, smugly No, seriously, that includes yours. — this guy, jaded
- 10. @jschaumaO’Reilly Security 2017 $ units You have: a huge infrastructure with lots of baggage You want: a unified ingress serving platform * lots of work across tons of teams / 0 Floating point exception (core dumped) $
- 11. @jschaumaO’Reilly Security 2017 $ units You have: an https service You want: to accept end-user traffic from the internet - keep up with changing requirements - implement critical updates across all systems in <24h - run latest stable release of supported software - implement non-critical updates within <3 months $
- 12. Be f*ckin explicit about general things. @jschaumaO’Reilly Security 2017
- 13. Be f*ckin explicit about general things. (Common sense ain’t.) @jschaumaO’Reilly Security 2017
- 14. @jschaumaO’Reilly Security 2017 $ units You have: …uhm, good question ^C $
- 15. @jschaumaO’Reilly Security 2017 - certificates with a Not Before date set prior to the Unix epoch (00:00:00, January 1st, 1970) - certificates with a Not Before date set in 2023 - certificates with a Not Before date set to ”110204212630-1200” - certificates with a Not After date set in 1902 - certificates expiring 10 years in the future - certificates expiring in 2100 - certificates expiring in the year 4752 - self-signed certificates galore - various properties having stood up their own CAs - key length of 512 - certificates with an MD5 signature - publicly used certificates that expired -15 years - cipher suites using a NULL encryption cipher - cipher suites using a NULL authentication cipher - cipher suites offering export ciphers - 14 different versions of OpenSSL - systems vulnerable to Heartbleed, POODLE, Logjam, FREAK, DROWN, and $SILLYNAME - certificates with ~200 SANs - certificates without either a CN or a SAN - certificates with a CN of "*" Weird things we found:
- 16. Any sufficiently large infrastructure is indistinguishable from the internet. @jschaumaO’Reilly Security 2017
- 18. One in a million is next Tuesday every couple of minutes. @jschaumaO’Reilly Security 2017 https://blogs.msdn.microsoft.com/larryosterman/2004/03/30/one-in-a-million-is-next-tuesday/
- 19. The lowest common denominator will always drag you down. @jschaumaO’Reilly Security 2017
- 20. The lowest common denominator internet of unpatchable crap will always drag you down. @jschaumaO’Reilly Security 2017
- 21. IoT is when “smart” means “dumb”. @jschaumaO’Reilly Security 2017 https://www.philips.com/a-w/mobile-privacy-notice/smart-shaver-app.html
- 22. @jschaumaO’Reilly Security 2017 TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256 TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384 TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256 TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384 TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA TLS_RSA_WITH_AES_128_GCM_SHA256 TLS_RSA_WITH_AES_256_GCM_SHA384 TLS_RSA_WITH_AES_128_CBC_SHA256 TLS_RSA_WITH_AES_256_CBC_SHA256 TLS_RSA_WITH_AES_128_CBC_SHA TLS_RSA_WITH_AES_256_CBC_SHA ECDSA missing - coming soon! ChaCha20/Poly1305 missing - coming soon! Prefer Forward Secrecy Prefer GCM over CBC Prefer faster “good enough” over slower, stronger.
- 23. @jschaumaO’Reilly Security 2017 Lowest common denominator is low… https://github.com/jschauma/cipherdiff
- 24. @jschaumaO’Reilly Security 2017 $ units You have: an x509 certificate You want: to accept end-user traffic from the internet - be issued by approved CA - have Certificate Transparency - RSA keys >= 2048; ECDSA >= 256 - misc. CN/SAN restrictions - validity <= 6 months $
- 27. If it hurts, do it more often. @jschaumaO’Reilly Security 2017 https://www.martinfowler.com/bliki/FrequencyReducesDifficulty.html
- 29. @jschaumaO’Reilly Security 2017 #Infosec Minimum Viable Protection
- 30. 1) get buy-in from exec. @jschaumaO’Reilly Security 2017
- 31. 0) get pwned 1) get buy-in from exec. @jschaumaO’Reilly Security 2017 https://www.netmeister.org/blog/crazy-like-a-fox.html
- 32. 0) get pwned 1) get buy-in from exec. 2) incremental changes @jschaumaO’Reilly Security 2017
- 33. Perfect is the enemy of the good. "Eh, good enough." is the enemy of actually good. @jschaumaO’Reilly Security 2017
- 34. 0) get pwned 1) get buy-in from exec. 2) incremental changes 3) sell something @jschaumaO’Reilly Security 2017
- 36. @jschaumaO’Reilly Security 2017 Patience, young skywalker.
- 37. 0) get pwned 1) get buy-in from exec. 2) incremental changes 3) sell something 4) profit @jschaumaO’Reilly Security 2017
- 39. 0) get pwned 1) get buy-in from exec. 2) incremental changes 3) sell something 4) profit @jschaumaO’Reilly Security 2017
- 41. 0) get pwned 1) get buy-in from exec. 2) incremental changes 3) sell something 4) profit goto 2 @jschaumaO’Reilly Security 2017
- 42. @jschaumaO’Reilly Security 2017 “We fight for the user. We must do better today that we did yesterday, and better tomorrow than we did today.” — Chris Nims, CISO / Chief Paranoid at Oath
- 43. @jschaumaO’Reilly Security 2017 Things to come: - ECDSA - Expect-CT - OpenSSL 1.1 (ChaCha20/Poly1305) - OCSP Must-Staple - shorter validity - apply to all Oath brands
- 44. Fake it 'till you make it. @jschaumaO’Reilly Security 2017 Effecting change
- 45. Chokepoints and defaults are your secret weapon. @jschaumaO’Reilly Security 2017 Effecting change
- 46. First: fix the future. @jschaumaO’Reilly Security 2017 Effecting change
- 47. Lead by example, but offer autonomy. @jschaumaO’Reilly Security 2017 Effecting change
- 48. Know what might break before you hit ‘go’. @jschaumaO’Reilly Security 2017 Effecting change
- 49. Transparency goes a long way. @jschaumaO’Reilly Security 2017 Effecting change
- 50. Incremental changes. Always move forward. Lead by example, be transparent. Encourage autonomy. We can’t reach 100% security, but we can always improve. @jschaumaO’Reilly Security 2017 How to be boring:
- 51. Apache Traffic Server Google Chrome Team Mozilla Observatory SSLLabs Yahoo Edge Team (Yahoo/Oath/All) Paranoids Credits @jschaumaO’Reilly Security 2017