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Heartbleed 
Nick Sullivan (@grittygrease) 
Friday, August 8, 2014
Overview 
• What is Heartbleed? 
• The Heartbleed Challenge 
• How certificate revocation is broken 
and endangered our network 
2
Application Layer - CloudFlare 
• DNS (TCP & UDP port 53) 
• HTTP (TCP port 80) 
• HTTPS (TCP port 443) - powered by OpenSSL 
3
Heartbleed 
• A bug so bad it has its own website 
and branding 
4
What is it? 
• A bug in OpenSSL 1.0.1 
! 
• Changelog 
• Major changes between OpenSSL 1.0.0h and OpenSSL 1.0.1 [14 Mar 2012]: 
• TLS/DTLS heartbeat support. 
5
What is a heartbeat? 
• Heartbeat: a keepalive extension to TLS 
! 
• Client sends (length, challenge) 
• Server sends (length, challenge) 
6
What was the bug? 
• Classic buffer over-read 
• Attacker sends length value 
that is too long 
• Server returns attacker supplied 
amount of memory (up to 64kB) 
7
8
Why was it so dangerous? 
• One request gets attacker server data 
• Typically not logged — doesn’t leave a trace 
• Valuable information 
• Random decrypted data 
• Login session cookies 
• SSL/TLS private keys (???) 
9
Who was vulnerable? 
10
Who was vulnerable? 
• Any server running OpenSSL 
• Apache and nginx use OpenSSL by default: 65% of all active sites 
! 
! 
• 0.8% of the top 200,000 still vulnerable (May 2, 2014) 
11
Who was impacted? 
• Almost everybody 
12
Who discovered it? 
• Neel Mehta at Google 
• Codenomicon 
! 
• Sometime in March 2014 or earlier 
13
Disclosure — keeping it secret 
• CloudFlare, Google, Akamai, Facebook, others were notified early 
• Why: large web-facing networks with the largest impact(?) 
! 
• Encrypted communication 
• Source code visibility restricted to need-to-know 
• Secure software upgrade 
14
Big Questions 
• Were private keys at risk? 
• Do I have to revoke all my certificates? 
15
The CloudFlare Heartbleed challenge 
• Can someone really steal private keys from nginx? 
• Code said probably not 
• Temporary variables cleaned up 
• Private key allocated earlier 
! 
• We set up a challenge on https://www.cloudflarechallenge.com/heartbleed 
16
The CloudFlare Heartbleed challenge 
! 
! 
! 
• Results: solved in under 10 hours 
• Private keys are vulnerable 
• Server had 200Mbps of “mystery” outbound traffic 
17
18
RSA 
• Two prime numbers P & Q 
• Public key, including P x Q 
• Finding P or Q can get you the private key 
19
How it was solved 
• Take every 128byte block 
• Attempt to divide into public RSA key 
! 
• Coppersmith’s attack (only requires partial prime factor) 
20
How it was solved 
• Why was the private key on the heap? 
• There was a second bug in OpenSSL 
! 
• The prime factor was used in the computation in a temporary variable 
• Temporary variables were not cleaned during a resize 
21
Challenge aftermath 
• Undeniable key compromise potential 
• All certificates need to be revoked and re-keyed 
! 
• CloudFlare revoked over 100,000 certificates 
22
How revocation works 
• Certificate Revocation Lists (CRLs) 
• Online Certificate Status Protocol (OCSP) 
• CRLSets (Google Chrome proprietary) 
23
Revoking 100,000 SSL certificates in 24 hours 
24
Revoking 100,000 SSL certificates in 24 hours 
25
Revoking 100,000 SSL certificates in 24 hours 
• CRL for GlobalSign grew from 22KB to 4.7MB 
• CloudFlare provides caching for these CRLs 
• We started seeing 30Gbps extra baseline traffic 
• Repeated waves of 100Gbps every three hours (24 hours below) 
26
Revoking 100,000 SSL certificates in 24 hours 
• The issue: CRL was being downloaded by web browsers 
• New CRL was being published on a 1-3 hour basis 
• Internet Explorer 7/8 downloads CRLs, 9/10 OCSP with CRL fallback 
• OS X: OCSP with CRL fallback 
• No delta updates, we downloaded the whole thing 
27
Revoking 100,000 SSL certificates in 24 hours 
• Intra-machine links were being congested 
• Had to modify cache strategy 
• Moved from one cache box per rack to caching on all boxes 
• Update cache headers to increase browser cache time 
• Asked CA to give CloudFlare their own intermediate certificate 
28
Revocation is broken 
• None of 100,000+ certificates were in Chrome’s CRLSets 
• CRL growth can’t scale 
• Too many cases when OCSP hard fail 
29
Revocation is broken 
• Most efficient revocation code ever: 
30
Revocation solutions? 
• Shorter certificate expiration periods 
• CRL lists not necessary after expiration 
• OCSP Must-staple 
• Server performs OCSP check and sends to client when connecting 
31
Conclusion 
• Bug in pervasive server software 
• Huge unexpected impact on Internet security 
• Crowdsourcing works 
• Revocation shown to be problematic 
32
Heartbleed 
Nick Sullivan (@grittygrease) 
Friday, August 8, 2014

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Sullivan heartbleed-defcon22 2014

  • 1. Heartbleed Nick Sullivan (@grittygrease) Friday, August 8, 2014
  • 2. Overview • What is Heartbleed? • The Heartbleed Challenge • How certificate revocation is broken and endangered our network 2
  • 3. Application Layer - CloudFlare • DNS (TCP & UDP port 53) • HTTP (TCP port 80) • HTTPS (TCP port 443) - powered by OpenSSL 3
  • 4. Heartbleed • A bug so bad it has its own website and branding 4
  • 5. What is it? • A bug in OpenSSL 1.0.1 ! • Changelog • Major changes between OpenSSL 1.0.0h and OpenSSL 1.0.1 [14 Mar 2012]: • TLS/DTLS heartbeat support. 5
  • 6. What is a heartbeat? • Heartbeat: a keepalive extension to TLS ! • Client sends (length, challenge) • Server sends (length, challenge) 6
  • 7. What was the bug? • Classic buffer over-read • Attacker sends length value that is too long • Server returns attacker supplied amount of memory (up to 64kB) 7
  • 8. 8
  • 9. Why was it so dangerous? • One request gets attacker server data • Typically not logged — doesn’t leave a trace • Valuable information • Random decrypted data • Login session cookies • SSL/TLS private keys (???) 9
  • 11. Who was vulnerable? • Any server running OpenSSL • Apache and nginx use OpenSSL by default: 65% of all active sites ! ! • 0.8% of the top 200,000 still vulnerable (May 2, 2014) 11
  • 12. Who was impacted? • Almost everybody 12
  • 13. Who discovered it? • Neel Mehta at Google • Codenomicon ! • Sometime in March 2014 or earlier 13
  • 14. Disclosure — keeping it secret • CloudFlare, Google, Akamai, Facebook, others were notified early • Why: large web-facing networks with the largest impact(?) ! • Encrypted communication • Source code visibility restricted to need-to-know • Secure software upgrade 14
  • 15. Big Questions • Were private keys at risk? • Do I have to revoke all my certificates? 15
  • 16. The CloudFlare Heartbleed challenge • Can someone really steal private keys from nginx? • Code said probably not • Temporary variables cleaned up • Private key allocated earlier ! • We set up a challenge on https://www.cloudflarechallenge.com/heartbleed 16
  • 17. The CloudFlare Heartbleed challenge ! ! ! • Results: solved in under 10 hours • Private keys are vulnerable • Server had 200Mbps of “mystery” outbound traffic 17
  • 18. 18
  • 19. RSA • Two prime numbers P & Q • Public key, including P x Q • Finding P or Q can get you the private key 19
  • 20. How it was solved • Take every 128byte block • Attempt to divide into public RSA key ! • Coppersmith’s attack (only requires partial prime factor) 20
  • 21. How it was solved • Why was the private key on the heap? • There was a second bug in OpenSSL ! • The prime factor was used in the computation in a temporary variable • Temporary variables were not cleaned during a resize 21
  • 22. Challenge aftermath • Undeniable key compromise potential • All certificates need to be revoked and re-keyed ! • CloudFlare revoked over 100,000 certificates 22
  • 23. How revocation works • Certificate Revocation Lists (CRLs) • Online Certificate Status Protocol (OCSP) • CRLSets (Google Chrome proprietary) 23
  • 24. Revoking 100,000 SSL certificates in 24 hours 24
  • 25. Revoking 100,000 SSL certificates in 24 hours 25
  • 26. Revoking 100,000 SSL certificates in 24 hours • CRL for GlobalSign grew from 22KB to 4.7MB • CloudFlare provides caching for these CRLs • We started seeing 30Gbps extra baseline traffic • Repeated waves of 100Gbps every three hours (24 hours below) 26
  • 27. Revoking 100,000 SSL certificates in 24 hours • The issue: CRL was being downloaded by web browsers • New CRL was being published on a 1-3 hour basis • Internet Explorer 7/8 downloads CRLs, 9/10 OCSP with CRL fallback • OS X: OCSP with CRL fallback • No delta updates, we downloaded the whole thing 27
  • 28. Revoking 100,000 SSL certificates in 24 hours • Intra-machine links were being congested • Had to modify cache strategy • Moved from one cache box per rack to caching on all boxes • Update cache headers to increase browser cache time • Asked CA to give CloudFlare their own intermediate certificate 28
  • 29. Revocation is broken • None of 100,000+ certificates were in Chrome’s CRLSets • CRL growth can’t scale • Too many cases when OCSP hard fail 29
  • 30. Revocation is broken • Most efficient revocation code ever: 30
  • 31. Revocation solutions? • Shorter certificate expiration periods • CRL lists not necessary after expiration • OCSP Must-staple • Server performs OCSP check and sends to client when connecting 31
  • 32. Conclusion • Bug in pervasive server software • Huge unexpected impact on Internet security • Crowdsourcing works • Revocation shown to be problematic 32
  • 33. Heartbleed Nick Sullivan (@grittygrease) Friday, August 8, 2014