1. HTTPS in 2015 Eric Lawrence @ericlaw

2. Quick Introductions Eric Lawrence @ericlaw

3. Why? Bad guys Government snoops Non-neutral networks (Gogo, corporate) “Value adding providers” Rewards Increased user trust Better search ranking More reliable egress (HTTP2; WebSocket)

4. The Stack Your Client Browser HTTP SSL/TLS TCP IP

5. HTTPS Provides… Authentication Confidentiality Integrity

6. How? Public Key Infrastructure for certificate chains Public Key Cryptography for key exchanges Symmetric Cryptography for data transfers

7. Certificates

8. Hash Algorithms MD5 busted SHA1 heading that way SHA256 entering mainstream in 2015

9. Validating the Certificate Validate certificate signature Validate it is within validity period Validate it chains to trusted root Validate Subject CN or SubjectAltName contains hostname of the target… – Wildcards Check to see if it was revoked

10. Extended Validation SSL BankoftheVVest.com phishing site Domain validation and the race to the bottom

11. Ciphers, Hashes, and MACs oh my…

12. Initial Handshake

14. SNI Extension Break the IPEndpoint->Server mapping Important to allow HTTPS virtual hosting Not available on WinXP or Android < v2.3 

16. Forward Secrecy If you can record ALL of the traffic… And you’re using RSA… And you can ever steal or crack the private key (at any point in the future… Achieving Forward Secrecy Do not use the RSA key exchange, which does not provide forward secrecy. Instead, look for the string ECDHE or DHE in the cipher suite name. RSA can be used for key exchange and authentication; there is nothing wrong with the latter. 

17. Popular Ciphers Triple-DES RC4 AES ChaCha (new)

18. Revocation CRL (Certificate Revocation List) OCSP (Online Certificate Status Protocol) Deployed blocklists

19. Certificate Pinning Built-into browser Distributed with security software like Microsoft EMET New HTTP Public Key Pinning header https://tools.ietf.org/html/draft- ietf-websec-key-pinning-21 https://tools.ietf.org/html/draft- ietf-websec-key-pinning-21 Public-Key-Pins: pin- sha256="GHI..."; pin- sha256="JKL..."; max-age=… report-uri=…; includeSubDomains

20. Certificate Transparency http://www.certificate-transparency.org/ Google Chrome intends to require Certificate Transparency (CT) for all EV certificates issued after 2014. A SCT “Signed Certificate Timestamp” is added to the certificate.

21. Performance

22. https://www.youtube.com/watch?v=0EB7zh_7UE4

24. Session Resumption http://calendar.perfplanet.com/2014/speeding-up-https-with-session-resumption/

25. ECC Public Keys ECC certificates offer stronger security and smaller certificates - e.g. a 256-bit ECC key is equivalent to a 3072-bit RSA key.stronger security and smaller certificates http://arstechnica.com/security/2013/10/a-relatively-easy-to-understand-primer-on-elliptic-curve-cryptography/

26. Run Latest Versions

27. I’m in!

30. Enabling HTTPS for your site will be as easy as installing a small piece of certificate management software on the server: https://example.com is immediately live. The Let’s Encrypt management software will: Automatically prove to the Let’s Encrypt CA that you control the website Obtain a browser-trusted certificate and set it up on your web server Keep track of when your certificate is going to expire, and automatically renew it Help you revoke the certificate if that ever becomes necessary. No validation emails, no complicated configuration editing, no expired certificates breaking your website. And of course, because Let’s Encrypt provides certificates for free, no need to arrange payment.

31. WebDev Errors Critical Mistake #1: Non-HTTPS Login pages (even if submitting to a HTTPS page).

32. WebDev Errors Critical Mistake #2: Mixing HTTP Content into a HTTPS page

33. HSTS

34. http://blogs.msdn.com/b/ieinternals/archive/2014/08/18/hsts-strict-transport-security- attacks-mitigations-deployment-https.aspx Insecure references are upgraded Certificate errors are fatal Use the HTTPS response header: Strict-Transport-Security: max-age=63072000; includeSubDomains Or get on the browsers’ pre-load list (avoid bootstrapping problem)

35. Fiddler Visualization If there’s an exclamation point in the column, you’ve done something wrong!

36. Migration Guide https://t.co/0ORIlnp64Y https://t.co/0ORIlnp64Y Chris Palmer @fugueish Use STS Use Secure attribute on cookies Protocol-relative URLs Run the Qualys SSLLabs Server test

37. SSLLabs

38. HTTPS all the Things!

39. Best Practice Secure everything. It’s very hard to predict future attack scenarios. Yes, really.

40. HTTP Content indicator

42. Not Just Browsers…

43. Hacks

47. HTTPS Traffic Analysis Source IP Destination IP Server Name (via SNI) Higher-level protocol (via ALPN) Client Certificates (if sent before encryption)

49. Implementation Issues Truncation Compression Clickthrough UI

50. Implementation Issues Truncation Compression Clickthrough UI

51. Implementation Issues Truncation Compression Clickthrough UI

52. MITM/MITB Attacks

54. Extended Validation Won’t Help

57. Heartbleed http://xkcd.com/1354/

58. Sometimes, you do attack the crypto

59. Crypto Deep Dive later this morning…

60. Book: Bulletproof SSL and TLS https://www.feistyduck.com/books/bulletproof-ssl-and-tls/ Coupon Code for 25% off CODEMASH Valid January 1st to 31st Free Chapter: https://www.feistyduck.com/books/openssl-cookbook/

61. Thanks for coming! Questions? Find me on Twitter: @ericlaw Email me: e_Lawrence@hotmail.com Go forth and secure all the things!

62. See how lightsabers are built…

63. Combatting breach?