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Масштабируя TLS / Артём Гавриченков (Qrator Labs)

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The document provides a history of TLS and SSL developments, highlighting key milestones such as the introduction of SPDY, HTTP/2, and Let's Encrypt. It discusses the role of certificate authorities (CAs) and issues surrounding Wosign, emphasizing the importance of security practices in certificate management. Additionally, it covers best practices for TLS deployment, the evolution of AES encryption, and the significance of perfect forward secrecy in enhancing data security.

Engineering
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Масштабируя TLS Артём Гавриченков <ximaera@qrator.net>
Краткая история нового времени • 2010: SPDY w/de-facto mandatory* SSL/TLS • 2014: “HTTPS as a ranking signal” at Google • 2015: HTTP/2 w/de-facto mandatory* TLS • 2016: Let’s Encrypt * – https://forum.nginx.org/read.php?21,236132,236184 *– https://daniel.haxx.se/blog/2015/03/06/tls-in-http2/
Масштабируя TLS / Артём Гавриченков (Qrator Labs)
Масштабируя TLS / Артём Гавриченков (Qrator Labs)
Краткая история нового времени • 2010: SPDY w/de-facto mandatory* SSL/TLS • 2014: “HTTPS as a ranking signal” at Google • 2015: HTTP/2 w/de-facto mandatory* TLS • 2016: Let’s Encrypt * – https://forum.nginx.org/read.php?21,236132,236184 *– https://daniel.haxx.se/blog/2015/03/06/tls-in-http2/
Краткая история нового времени • 2010: SPDY w/de-facto mandatory* SSL/TLS • 2013: NSA story • 2014: “HTTPS as a ranking signal” at Google • 2014: • 2015: HTTP/2 w/de-facto mandatory* TLS • 2015: • 2016: Let’s Encrypt • 2016: * – https://forum.nginx.org/read.php?21,236132,236184 *– https://daniel.haxx.se/blog/2015/03/06/tls-in-http2/
Краткая история нового времени • 2010: SPDY w/de-facto mandatory* SSL/TLS • 2013: NSA story • 2014: “HTTPS as a ranking signal” at Google • 2014: Heartbleed, POODLE • 2015: HTTP/2 w/de-facto mandatory* TLS • 2015: RFC 7457 • 2016: Let’s Encrypt * – https://forum.nginx.org/read.php?21,236132,236184 *– https://daniel.haxx.se/blog/2015/03/06/tls-in-http2/
Масштабируя TLS / Артём Гавриченков (Qrator Labs)
Краткая история нового времени • 2010: SPDY w/de-facto mandatory* SSL/TLS • 2013: NSA story • 2014: “HTTPS as a ranking signal” at Google • 2014: Heartbleed, POODLE • 2015: HTTP/2 w/de-facto mandatory* TLS • 2015: RFC 7457 • 2016: Let’s Encrypt * – https://forum.nginx.org/read.php?21,236132,236184 *– https://daniel.haxx.se/blog/2015/03/06/tls-in-http2/
Краткая история нового времени • 2010: SPDY w/de-facto mandatory* SSL/TLS • 2013: NSA story • 2014: “HTTPS as a ranking signal” at Google • 2014: Heartbleed, POODLE • 2015: HTTP/2 w/de-facto mandatory* TLS • 2015: RFC 7457, FREAK, Logjam • 2016: Let’s Encrypt • 2016: DROWN * – https://forum.nginx.org/read.php?21,236132,236184 *– https://daniel.haxx.se/blog/2015/03/06/tls-in-http2/
SSL/TLS PKI • Root certificate authorities, trust chain
SSL/TLS PKI • Root certificate authorities, trust chain • 92 CAs in Firefox
SSL/TLS PKI • Root certificate authorities, trust chain • Trusted, because they make it for living • Independent from large corporations, government, etc.
SSL/TLS PKI • Root certificate authorities, trust chain • Trusted, because they make it for living • Independent from large corporations, government, etc. Except, some of them ARE government
SSL/TLS PKI • Root certificate authorities, trust chain • Trusted, because they make it for living • Independent from large corporations, government, etc. And some of them are large corporations Except, some of them ARE government
SSL/TLS PKI • Root certificate authorities, trust chain • Trusted, because they make it for living • Independent from large corporations, government, etc. • Pursuing their interests as trusted third parties
SSL/TLS PKI • Root certificate authorities, trust chain • Trusted, because they make it for living • Independent from large corporations, government, etc. • Pursuing their interests as trusted third parties • Corporations and government always tend to elevate their own interests
The story of WoSign • Trusted since 2009 • Aggressive marketing and free certificates • Passed audit by Ernst&Young
The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner
The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control
The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control • Allowed using subdomains to verify 2nd level domain
The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control • Allowed using subdomains to verify 2nd level domain • Allowed using arbitrary files to verify ownership
The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control • Allowed using subdomains to verify 2nd level domain • Allowed using arbitrary files to verify ownership • Allowed to issue certificates for arbitrary domains without verification
The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control • Allowed using subdomains to verify 2nd level domain • Allowed using arbitrary files to verify ownership • Allowed to issue certificates for arbitrary domains without verification • Issued backdated SHA-1 certificates
The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control • Allowed using subdomains to verify 2nd level domain • Allowed using arbitrary files to verify ownership • Allowed to issue certificates for arbitrary domains without verification • Issued backdated SHA-1 certificates • Used unpatched software (such as dig) on the validation server
The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control • Allowed using subdomains to verify 2nd level domain • Allowed using arbitrary files to verify ownership • Allowed to issue certificates for arbitrary domains without verification • Issued backdated SHA-1 certificates • Used unpatched software (such as dig) on the validation server • Purchased other CA (StartCom) and attempted to suppress information about the ownership transfer
The story of WoSign The aftermath?
The story of WoSign The aftermath? • Banned by Google in Chrome • Banned by Mozilla for a year
The story of WoSign The aftermath? • Banned by Google in Chrome • Banned by Mozilla for a year • Still trusted by Microsoft and lots of unpatched equipment
Aftermath • Go and choose the cheapest CA available • Bonus points if it provides some kind of API
Aftermath • Go and choose the cheapest CA available • Bonus points if it provides some kind of API • Pick multiple CAs
Aftermath • Go and choose the cheapest CA available • Bonus points if it provides some kind of API • Pick multiple CAs • “Extended validity” certificates?
Aftermath • Go and choose the cheapest CA available • Bonus points if it provides some kind of API • Pick multiple CAs • “Extended validity” certificates are a security theater (don’t bother if you are not a bank and auditor doesn’t force you to)
Aftermath • Go and choose the cheapest CA available • Bonus points if it provides some kind of API • Pick multiple CAs • “Extended validity” certificates are a security theater (don’t bother if you are not a bank and auditor doesn’t force you to) • Prefer short-lived certificates
Long-living certificates? Pros: • Discount • Less pain in the #^$ updating all the certs
Long-living certificates? Pros: • Discount • Less pain in the #^$ updating all the certs Cons: • Soft-fail CRL and OCSP are not reliable • Hard-fail CRL and OCSP are never used (you may do it in your app though) • Certificate deployment and management must be automated anyway
Long-living certificates? • CRL and OCSP are not reliable • Certificate deployment and management must be automated Long-lived cert is a technical debt. It wouldn’t punish you immediately. It will hurt you eventually.
Automated certificate management • Add, remove, change and revoke your certificates real quick • Manage certificates properly: short lifetime, multiple keys • Set up a clientside TLS auth
Automated certificate management • Add, remove, change and revoke your certificates real quick • Manage certificates properly: short lifetime, multiple keys • Set up a clientside TLS auth • Quickly work around obscure issues like “Intermediate CA was revoked”
The story of GlobalSign • During a planned maintenance, accidentally revoked its own certificate • Used CDN (Cloudflare) for CRL and OCSP • Undid revocation, but it’s got cached on CDN
The story of GlobalSign • During a planned maintenance, accidentally revoked its own certificate • Used CDN (Cloudflare) for CRL and OCSP • Undid revocation, but it’s got cached on CDN • Four days before cached response will expire in a browser • Wikipedia, Dropbox, Spotify, Financial Times affected • Large sites affected more because CRL got cached everywhere immediately
The story of GlobalSign • Large sites affected more because CRL got cached everywhere immediately • “All is good and yet traffic dropped by 30%” • Really hard to troubleshoot • The issue is of distributed nature • You depend on a vendor
The story of GlobalSign • Large sites affected more because CRL got cached everywhere immediately • “All is good and yet traffic dropped by 30%” • Really hard to troubleshoot • The issue is of distributed nature • You depend on a vendor • Multiple different certs from different vendors helped to track down • tcpdump also of a great help: sessions got stuck at TLS Server Hello
The story of GlobalSign • Really hard to troubleshoot • The issue is of distributed nature • You depend on a vendor • Multiple different certs from different vendors will help to track down • tcpdump also of a great help: sessions got stuck at TLS Server Hello TLS is still bleeding edge of technology. Unsufficient tools, unsufficient knowledge.
The story of GlobalSign • Really hard to troubleshoot • So, hours wasted before the root cause is found • The fix must be immediate => cert management automation!
Automated certificate management • CA with API
Automated certificate management • CA with API • Let’s Encrypt?
Automated certificate management • CA with API • Let’s Encrypt? Very good if you don’t need wildcard certificates.
Automated certificate management • CA with API • Let’s Encrypt? Very good if you don’t need wildcard certificates. • Tools like SSLMate • In-house plugins for ansible etc.
What to set up during the deployment?
What to set up during the deployment? • Strict Transport Security • “Opportunistic encryption” simply doesn’t work • Most users won’t notice if HTTPS is absent • HTTPS only makes sense if it’s enforced
What to set up during the deployment? • Strict Transport Security • “Opportunistic encryption” simply doesn’t work • Most users won’t notice if HTTPS is absent • HTTPS only makes sense if it’s enforced • Public Key Pinning • Pin all end-entity public keys • Create a backup • Include future leafs • Rotate often => use automated tools to generate the header
What to set up during the deployment? • Ciphers • https://wiki.mozilla.org/Security/TLS_Configurations
What to set up during the deployment? • Ciphers • https://wiki.mozilla.org/Security/TLS_Configurations outdated • https://mozilla.github.io/server-side-tls/ssl-config-generator/ • Update frequently (automation?)
What to set up during the deployment? • Ciphers • https://wiki.mozilla.org/Security/TLS_Configurations outdated • https://mozilla.github.io/server-side-tls/ssl-config-generator/ • Update frequently (automation?)
The story of Rijndael
The story of Rijndael (finally it sounds almost like Tolkien)
The story of Rijndael/AES • Ordered by U.S. federal government • Approved by NSA, 1998-2001 • Adopted by U.S. DoD and Army
The story of Rijndael/AES • Adopted by U.S. DoD and Army • Military required three distinct security levels, with less sensitive data to be encrypted using the most weak method and vice versa
The story of Rijndael/AES • Adopted by U.S. DoD and Army • Military required three distinct security levels, with less sensitive data to be encrypted using the most weak method and vice versa • Crypto designers implemented three key sizes (128, 192, 256), with the most weak still unbreakable in foreseeable future (except quantum computers)
The story of Rijndael/AES • Adopted by U.S. DoD and Army • Military required three distinct security levels, with less sensitive data to be encrypted using the most weak method and vice versa • Crypto designers implemented three key sizes (128, 192, 256), with the most weak still unbreakable in foreseeable future (except quantum computers) • So, AES-128 is still good enough • Not that it matters much with modern AES-NI
The story of Perfect Forward Secrecy • Present in ephemeral Diffie-Hellman ciphers
The story of Perfect Forward Secrecy • Present in ephemeral Diffie-Hellman ciphers • Makes out-of-path analysis impossible • Makes historic data analysis impossible
The story of Perfect Forward Secrecy • Present in ephemeral Diffie-Hellman ciphers • Makes out-of-path analysis impossible • Makes historic data analysis impossible • Good catch for an out-of-path DPI and/or WAF 70% HTTPS requests come and go without analysis
• Present in ephemeral Diffie-Hellman ciphers • Makes out-of-path analysis impossible • Makes historic data analysis impossible • Good catch for an out-of-path DPI and/or WAF 70% HTTP requests go without analysis The story of Perfect Forward Secrecy 60% legitimate 90% malicious
Protocols
Protocols • SSLv2 is dead
Protocols • SSLv2 is dead • SSLv3 is dead* • TLSv1.0 is dead * – if you don’t have to serve content to IE6 or a TV set
Protocols • SSLv2 is dead • SSLv3 is dead* • TLSv1.0 is dead • TLS is alive and growing * – if you don’t have to serve content to IE6 or a TV set
Protocols • SSLv2 is dead • SSLv3 is dead* • TLSv1.0 is dead • TLS is alive and growing • Maybe too fast: TLSv1.2 allowed DDoSCoin * – if you don’t have to serve content to IE6 or a TV set
Misc • OCSP stapling • Persistent connections (TLS handshake is expensive) • Fight unencrypted content!
Sound Bytes • Use short-lived certificates! • Automate! • Trust Mozilla! :-)
Q&A mailto: ximaera@qrator.net
Bonus track • Client certificates
Bonus track • Client certificates • May be combined with 2FA
Bonus track • Client certificates • May be combined with 2FA • May be integrated into certain applications as well • Unsupported by some mobile browsers OOTB :-(

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Масштабируя TLS / Артём Гавриченков (Qrator Labs)

  • 2. Краткая история нового времени • 2010: SPDY w/de-facto mandatory* SSL/TLS • 2014: “HTTPS as a ranking signal” at Google • 2015: HTTP/2 w/de-facto mandatory* TLS • 2016: Let’s Encrypt * – https://forum.nginx.org/read.php?21,236132,236184 *– https://daniel.haxx.se/blog/2015/03/06/tls-in-http2/
  • 5. Краткая история нового времени • 2010: SPDY w/de-facto mandatory* SSL/TLS • 2014: “HTTPS as a ranking signal” at Google • 2015: HTTP/2 w/de-facto mandatory* TLS • 2016: Let’s Encrypt * – https://forum.nginx.org/read.php?21,236132,236184 *– https://daniel.haxx.se/blog/2015/03/06/tls-in-http2/
  • 6. Краткая история нового времени • 2010: SPDY w/de-facto mandatory* SSL/TLS • 2013: NSA story • 2014: “HTTPS as a ranking signal” at Google • 2014: • 2015: HTTP/2 w/de-facto mandatory* TLS • 2015: • 2016: Let’s Encrypt • 2016: * – https://forum.nginx.org/read.php?21,236132,236184 *– https://daniel.haxx.se/blog/2015/03/06/tls-in-http2/
  • 7. Краткая история нового времени • 2010: SPDY w/de-facto mandatory* SSL/TLS • 2013: NSA story • 2014: “HTTPS as a ranking signal” at Google • 2014: Heartbleed, POODLE • 2015: HTTP/2 w/de-facto mandatory* TLS • 2015: RFC 7457 • 2016: Let’s Encrypt * – https://forum.nginx.org/read.php?21,236132,236184 *– https://daniel.haxx.se/blog/2015/03/06/tls-in-http2/
  • 9. Краткая история нового времени • 2010: SPDY w/de-facto mandatory* SSL/TLS • 2013: NSA story • 2014: “HTTPS as a ranking signal” at Google • 2014: Heartbleed, POODLE • 2015: HTTP/2 w/de-facto mandatory* TLS • 2015: RFC 7457 • 2016: Let’s Encrypt * – https://forum.nginx.org/read.php?21,236132,236184 *– https://daniel.haxx.se/blog/2015/03/06/tls-in-http2/
  • 10. Краткая история нового времени • 2010: SPDY w/de-facto mandatory* SSL/TLS • 2013: NSA story • 2014: “HTTPS as a ranking signal” at Google • 2014: Heartbleed, POODLE • 2015: HTTP/2 w/de-facto mandatory* TLS • 2015: RFC 7457, FREAK, Logjam • 2016: Let’s Encrypt • 2016: DROWN * – https://forum.nginx.org/read.php?21,236132,236184 *– https://daniel.haxx.se/blog/2015/03/06/tls-in-http2/
  • 11. SSL/TLS PKI • Root certificate authorities, trust chain
  • 12. SSL/TLS PKI • Root certificate authorities, trust chain • 92 CAs in Firefox
  • 13. SSL/TLS PKI • Root certificate authorities, trust chain • Trusted, because they make it for living • Independent from large corporations, government, etc.
  • 14. SSL/TLS PKI • Root certificate authorities, trust chain • Trusted, because they make it for living • Independent from large corporations, government, etc. Except, some of them ARE government
  • 15. SSL/TLS PKI • Root certificate authorities, trust chain • Trusted, because they make it for living • Independent from large corporations, government, etc. And some of them are large corporations Except, some of them ARE government
  • 16. SSL/TLS PKI • Root certificate authorities, trust chain • Trusted, because they make it for living • Independent from large corporations, government, etc. • Pursuing their interests as trusted third parties
  • 17. SSL/TLS PKI • Root certificate authorities, trust chain • Trusted, because they make it for living • Independent from large corporations, government, etc. • Pursuing their interests as trusted third parties • Corporations and government always tend to elevate their own interests
  • 18. The story of WoSign • Trusted since 2009 • Aggressive marketing and free certificates • Passed audit by Ernst&Young
  • 19. The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner
  • 20. The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control
  • 21. The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control • Allowed using subdomains to verify 2nd level domain
  • 22. The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control • Allowed using subdomains to verify 2nd level domain • Allowed using arbitrary files to verify ownership
  • 23. The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control • Allowed using subdomains to verify 2nd level domain • Allowed using arbitrary files to verify ownership • Allowed to issue certificates for arbitrary domains without verification
  • 24. The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control • Allowed using subdomains to verify 2nd level domain • Allowed using arbitrary files to verify ownership • Allowed to issue certificates for arbitrary domains without verification • Issued backdated SHA-1 certificates
  • 25. The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control • Allowed using subdomains to verify 2nd level domain • Allowed using arbitrary files to verify ownership • Allowed to issue certificates for arbitrary domains without verification • Issued backdated SHA-1 certificates • Used unpatched software (such as dig) on the validation server
  • 26. The story of WoSign https://wiki.mozilla.org/CA:WoSign_Issues • Issued certificates not requested by domain owner • Allowed using non-privileged ports (>50,000) to verify domain control • Allowed using subdomains to verify 2nd level domain • Allowed using arbitrary files to verify ownership • Allowed to issue certificates for arbitrary domains without verification • Issued backdated SHA-1 certificates • Used unpatched software (such as dig) on the validation server • Purchased other CA (StartCom) and attempted to suppress information about the ownership transfer
  • 27. The story of WoSign The aftermath?
  • 28. The story of WoSign The aftermath? • Banned by Google in Chrome • Banned by Mozilla for a year
  • 29. The story of WoSign The aftermath? • Banned by Google in Chrome • Banned by Mozilla for a year • Still trusted by Microsoft and lots of unpatched equipment
  • 30. Aftermath • Go and choose the cheapest CA available • Bonus points if it provides some kind of API
  • 31. Aftermath • Go and choose the cheapest CA available • Bonus points if it provides some kind of API • Pick multiple CAs
  • 32. Aftermath • Go and choose the cheapest CA available • Bonus points if it provides some kind of API • Pick multiple CAs • “Extended validity” certificates?
  • 33. Aftermath • Go and choose the cheapest CA available • Bonus points if it provides some kind of API • Pick multiple CAs • “Extended validity” certificates are a security theater (don’t bother if you are not a bank and auditor doesn’t force you to)
  • 34. Aftermath • Go and choose the cheapest CA available • Bonus points if it provides some kind of API • Pick multiple CAs • “Extended validity” certificates are a security theater (don’t bother if you are not a bank and auditor doesn’t force you to) • Prefer short-lived certificates
  • 35. Long-living certificates? Pros: • Discount • Less pain in the #^$ updating all the certs
  • 36. Long-living certificates? Pros: • Discount • Less pain in the #^$ updating all the certs Cons: • Soft-fail CRL and OCSP are not reliable • Hard-fail CRL and OCSP are never used (you may do it in your app though) • Certificate deployment and management must be automated anyway
  • 37. Long-living certificates? • CRL and OCSP are not reliable • Certificate deployment and management must be automated Long-lived cert is a technical debt. It wouldn’t punish you immediately. It will hurt you eventually.
  • 38. Automated certificate management • Add, remove, change and revoke your certificates real quick • Manage certificates properly: short lifetime, multiple keys • Set up a clientside TLS auth
  • 39. Automated certificate management • Add, remove, change and revoke your certificates real quick • Manage certificates properly: short lifetime, multiple keys • Set up a clientside TLS auth • Quickly work around obscure issues like “Intermediate CA was revoked”
  • 40. The story of GlobalSign • During a planned maintenance, accidentally revoked its own certificate • Used CDN (Cloudflare) for CRL and OCSP • Undid revocation, but it’s got cached on CDN
  • 41. The story of GlobalSign • During a planned maintenance, accidentally revoked its own certificate • Used CDN (Cloudflare) for CRL and OCSP • Undid revocation, but it’s got cached on CDN • Four days before cached response will expire in a browser • Wikipedia, Dropbox, Spotify, Financial Times affected • Large sites affected more because CRL got cached everywhere immediately
  • 42. The story of GlobalSign • Large sites affected more because CRL got cached everywhere immediately • “All is good and yet traffic dropped by 30%” • Really hard to troubleshoot • The issue is of distributed nature • You depend on a vendor
  • 43. The story of GlobalSign • Large sites affected more because CRL got cached everywhere immediately • “All is good and yet traffic dropped by 30%” • Really hard to troubleshoot • The issue is of distributed nature • You depend on a vendor • Multiple different certs from different vendors helped to track down • tcpdump also of a great help: sessions got stuck at TLS Server Hello
  • 44. The story of GlobalSign • Really hard to troubleshoot • The issue is of distributed nature • You depend on a vendor • Multiple different certs from different vendors will help to track down • tcpdump also of a great help: sessions got stuck at TLS Server Hello TLS is still bleeding edge of technology. Unsufficient tools, unsufficient knowledge.
  • 45. The story of GlobalSign • Really hard to troubleshoot • So, hours wasted before the root cause is found • The fix must be immediate => cert management automation!
  • 47. Automated certificate management • CA with API • Let’s Encrypt?
  • 48. Automated certificate management • CA with API • Let’s Encrypt? Very good if you don’t need wildcard certificates.
  • 49. Automated certificate management • CA with API • Let’s Encrypt? Very good if you don’t need wildcard certificates. • Tools like SSLMate • In-house plugins for ansible etc.
  • 50. What to set up during the deployment?
  • 51. What to set up during the deployment? • Strict Transport Security • “Opportunistic encryption” simply doesn’t work • Most users won’t notice if HTTPS is absent • HTTPS only makes sense if it’s enforced
  • 52. What to set up during the deployment? • Strict Transport Security • “Opportunistic encryption” simply doesn’t work • Most users won’t notice if HTTPS is absent • HTTPS only makes sense if it’s enforced • Public Key Pinning • Pin all end-entity public keys • Create a backup • Include future leafs • Rotate often => use automated tools to generate the header
  • 53. What to set up during the deployment? • Ciphers • https://wiki.mozilla.org/Security/TLS_Configurations
  • 54. What to set up during the deployment? • Ciphers • https://wiki.mozilla.org/Security/TLS_Configurations outdated • https://mozilla.github.io/server-side-tls/ssl-config-generator/ • Update frequently (automation?)
  • 55. What to set up during the deployment? • Ciphers • https://wiki.mozilla.org/Security/TLS_Configurations outdated • https://mozilla.github.io/server-side-tls/ssl-config-generator/ • Update frequently (automation?)
  • 56. The story of Rijndael
  • 57. The story of Rijndael (finally it sounds almost like Tolkien)
  • 58. The story of Rijndael/AES • Ordered by U.S. federal government • Approved by NSA, 1998-2001 • Adopted by U.S. DoD and Army
  • 59. The story of Rijndael/AES • Adopted by U.S. DoD and Army • Military required three distinct security levels, with less sensitive data to be encrypted using the most weak method and vice versa
  • 60. The story of Rijndael/AES • Adopted by U.S. DoD and Army • Military required three distinct security levels, with less sensitive data to be encrypted using the most weak method and vice versa • Crypto designers implemented three key sizes (128, 192, 256), with the most weak still unbreakable in foreseeable future (except quantum computers)
  • 61. The story of Rijndael/AES • Adopted by U.S. DoD and Army • Military required three distinct security levels, with less sensitive data to be encrypted using the most weak method and vice versa • Crypto designers implemented three key sizes (128, 192, 256), with the most weak still unbreakable in foreseeable future (except quantum computers) • So, AES-128 is still good enough • Not that it matters much with modern AES-NI
  • 62. The story of Perfect Forward Secrecy • Present in ephemeral Diffie-Hellman ciphers
  • 63. The story of Perfect Forward Secrecy • Present in ephemeral Diffie-Hellman ciphers • Makes out-of-path analysis impossible • Makes historic data analysis impossible
  • 64. The story of Perfect Forward Secrecy • Present in ephemeral Diffie-Hellman ciphers • Makes out-of-path analysis impossible • Makes historic data analysis impossible • Good catch for an out-of-path DPI and/or WAF 70% HTTPS requests come and go without analysis
  • 65. • Present in ephemeral Diffie-Hellman ciphers • Makes out-of-path analysis impossible • Makes historic data analysis impossible • Good catch for an out-of-path DPI and/or WAF 70% HTTP requests go without analysis The story of Perfect Forward Secrecy 60% legitimate 90% malicious
  • 68. Protocols • SSLv2 is dead • SSLv3 is dead* • TLSv1.0 is dead * – if you don’t have to serve content to IE6 or a TV set
  • 69. Protocols • SSLv2 is dead • SSLv3 is dead* • TLSv1.0 is dead • TLS is alive and growing * – if you don’t have to serve content to IE6 or a TV set
  • 70. Protocols • SSLv2 is dead • SSLv3 is dead* • TLSv1.0 is dead • TLS is alive and growing • Maybe too fast: TLSv1.2 allowed DDoSCoin * – if you don’t have to serve content to IE6 or a TV set
  • 71. Misc • OCSP stapling • Persistent connections (TLS handshake is expensive) • Fight unencrypted content!
  • 72. Sound Bytes • Use short-lived certificates! • Automate! • Trust Mozilla! :-)
  • 74. Bonus track • Client certificates
  • 75. Bonus track • Client certificates • May be combined with 2FA
  • 76. Bonus track • Client certificates • May be combined with 2FA • May be integrated into certain applications as well • Unsupported by some mobile browsers OOTB :-(

Editor's Notes

  • #2: Не туториал Как говорил Сергей Дмитриевич Кузнецов, … Настраивайте свой Nginx сами Общий взгляд на проблематику и возможности для решения проблем
  • #3: Связь между NSA и HTTPS в Google: шифрование внутренних коммуникаций
  • #5: Letsencrypt crowdfunding
  • #7: Связь между NSA и HTTPS в Google: шифрование внутренних коммуникаций
  • #9: Оптимизм IETF
  • #11: История про технологическую задолженность: Шифрование сделали, потому что хотелось Когда реально стало нужно, пришлось исправлять косяки Главный косяк – информированность Давайте пройдёмся по процессу и разберём основные моменты с акцентом на крупном сетапе Начнём с банальностей. Чтобы настроить шифрование, нужен сертификат. Сертификат надо купить. У кого?
  • #12: ЦС вы можете выбрать, и выбор у вас большой
  • #18: Как так? А перестать быть CA вообще сложно
  • #20: 13 проблем Вы не можете получить серт для чужого домена, нужно пройти валидацию alicdn
  • #22: Исследователи смогли получить валидный подписанный сертификат для github
  • #23: Исследователи смогли получить сертификат для Google и Facebook
  • #25: Задним числом
  • #30: Большие CA становятся too big to fail Есть альтернатива в виде DANE, но у неё есть инфраструктурные проблемы (задержки и пр.) и её вроде бы сложно внедрить везде
  • #32: Всё равно куча балансеров Один купите у Symantec, другой у Unizeto, третий возьмите бесплатно у LE – не сильно скажется на OPEX
  • #33: На EV не смотрят пользователи (кроме гиков), в него не верят компании, его даже не все браузеры умеют демонстрировать
  • #34: На EV не смотрят пользователи (кроме гиков), в него не верят компании, его даже не все браузеры умеют демонстрировать
  • #35: Диверсификация
  • #37: CRL и OCSP работают только тогда, когда не нужны. Адам Лэнгли сравнил их с ремнём безопасности, который рвётся в случае аварии
  • #38: Это костыль и долг. Его не придётся выплачивать сразу, но пол у вас под ногами становится чуть более зыбким
  • #43: Неведомая проклятая ерунда
  • #44: Помогает траблшутить, если у вас на разных балансерах разные серты – GlobalSign фейлится, видна корреляция Дополнительный плюс: если утекает ключ, то известно, с какого балансера, проще делать RCA Распределённых сервисов проверки CRL/OCSP нет Некоторые идеологии развёртывания вообще постулируют, что закрытый ключ не должен покидать машину, на которой он сгенерирован. Это технофашизм, конечно, но.
  • #49: Подумайте: может быть, они вам и не нужны? В 80% случаев wildcard берут для экономии, но LE бесплатен
  • #50: Подумайте: может быть, wildcard вам и не нужен? Итак, это 50-й слайд, и мы наконец смогли купить сертификат. Как же его настраивать?
  • #51: Итак, это 50-й слайд, и мы наконец смогли купить сертификат. Как же его настраивать?
  • #52: MUST
  • #55: Проверяйте эту страницу часто, если у вас нет штатного криптографа (хотя что вы тогда здесь делаете) – у Mozilla криптографы есть Don’t roll/invent your own crypto – золотое правило криптографии работает как в dev, так и в ops Некоторые моменты в конфигурации контринтуитивны
  • #56: Некоторые моменты в конфигурации контринтуитивны Поднимите руки, кто знает, почему так
  • #66: “Пакет Яровой”
  • #69: Technical debt! PCI-DSS Council
  • #70: Останавливаемся и вздыхаем: SSLv* уязвим TLSv* не поддерживается в TV
  • #71: Proof of work для blockchain Technical debt!
  • #72: Но если stapling сломается – всё плохо, hard-fail