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Managing Certificates and TLS Endpoints

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TLS/SSL is ubiquitous nowadays and is widely used to protect traffic on the Internet. Although TLS/SSL originated to protect web sites, it is now also being used for email, web services and VPNs among others. Yet, despite its widespread adoption, it is still difficult to keep track of the constantly emerging vulnerabilities that affect it. If not monitored, certificates can expire and new attacks are discovered even for mainstream ciphers and hashing algorithms. Add to that accidental server misconfigurations, unpatched systems, and flawed implementations, and the task of keeping systems current can become daunting. To make matters worse, commonly-used server configurations can be deprecated in major browsers/clients, breaking backwards-compatibility, providing a worse user experience for some, and leaving product maintainers scrambling to update certificates and settings quickly. For all these reasons, systems need constant vigilance to keep them up to date. This session will examine some steps which can be taken to keep up with the constantly changing landscape and demonstrate a few tools which can help manage and automate necessary updates to TLS/SSL endpoints.

This deck was originally presented at LASCON 2015: https://lascon2015.sched.org/event/4D3G/managing-certificates-and-tls-endpoints

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Managing Certificates and TLS Endpoints

  1. 1. Managing Certificates and TLS Endpoints Charles Neill & Henry Yamauchi Security Engineering Rackspace Hosting
  2. 2. • Charles Neill & Henry Yamauchi of the Security Engineering team at Rackspace • Tasked with managing a large number of TLS/SSL endpoints • Since Heartbleed, everyone's eyes are on TLS/SSL • Many headaches later, we now have a tool called TLSManager to help us out! (More on that later) www.rackspace.com 2 What's this all about?
  3. 3. • Wire encryption protocol • Provides authentication, integrity and confidentiality • Based on Public Key Infrastructure (PKI) • SSL originally designed at Netscape for eCommerce in the early-mid 1990’s – SSLv1 was never released, leaving us with SSLv2 and v3 + TLSv1.0, 1.1, and 1.2 today • Widely deployed on a variety of devices (smart phones, laptops, servers, appliances, etc.) • Deceptively simple to get started with (but can be much harder to maintain) www.rackspace.com 3 What is TLS/SSL?
  4. 4. • Time is fast approaching where TLS/SSL will be mandatory • Browsers beginning to warn users about sites not using TLS/SSL Firefox Chrome • Encryption overhead, cost are no longer valid excuses – Initiatives like Let's Encrypt (letsencrypt.org) are aiming to provide a free SSL certificate authority very soon to provide free certificates for all • Despite becoming easier/cheaper to set up, TLS/SSL can't just be turned on and left alone in most cases, as we'll see… www.rackspace.com 4 TLS adoption is increasing
  5. 5. •Email •IRC •APIs and web services •VPN •Appliances (load balancers, proxies, etc) •Smart phone apps www.rackspace.com 5 TLS/SSL not just for web servers
  6. 6. •Certificate Authorities (CAs) •Protocols •Ciphers •Key exchange •Key sizes •Hashes •Random Number Generators (RNGs) www.rackspace.com 6 TLS/SSL moving parts
  7. 7. • Multiple protocol versions (SSLv2, v3, TLSv1, v1.1, v1.2) • Certificates expire at different times • Server misconfiguration, multiple servers for single domain • Outdated systems • Large number of endpoints to keep track of www.rackspace.com 7 Issues managing TLS/SSL:
  8. 8. • Intermediate certs expire • Server certificates can accidentally get checked into version control and have to be revoked • Lax or compromised CAs may have to reissue their certs (e.g. Comodo attack) • Use of self-signed certificates www.rackspace.com 8 Also:
  9. 9. • New SSL vulnerabilities are discovered (e.g. POODLE) • Bugs in encryption software like OpenSSL or LibreSSL (e.g. Heartbleed) • Regulation compliance (e.g. PCI-DSS 3.1 will disallow TLSv1 in 2016) • SHA1 in certs will be flagged insecure in Jan 1st, 2017 (browser warnings now) www.rackspace.com 9 Oh, and don't forget:
  10. 10. 10www.rackspace.com
  11. 11. 11www.rackspace.com Ciphers
  12. 12. • When first connecting, client and server engage in negotiation • Client initially sends the cipher suites it supports • Server then (ideally) selects the strongest cipher that both supports • Server should be configured with only strong ciphers • There's a catch: the client essentially gets to decide what cipher is used by controlling the ciphers that they send to the server. In some man-in-the-middle attacks, the attacker can potentially downgrade ciphers in this way (e.g. LOGJAM). www.rackspace.com 12 TLS cipher negotiation
  13. 13. • Combination of encryption, MAC and key exchange algorithms • Available suites depend on the SSL/TLS version • TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256 ^ ^ ^ ^ | | | | | | | MAC hash algo | | Symmetric key attrs (algo, key size, mode) | Authentication algo Key exchange algo www.rackspace.com 13 Cipher suites
  14. 14. Recommended Avoid Key Exchange ECDHE_ECDSA DHE_RSA RSA NULL *_anon MAC Hash SHA384 SHA256 NULL MD5 SHA1 Ciphers AES_256_GCM AES_128_GCM AES_256_CBC AES_128_CBC NULL RC2_* RC4_* DES_* IDEA_* 3DES_* *_EXPORT_* www.rackspace.com 14 Cipher suite suggestions
  15. 15. 15www.rackspace.com Other configuration options
  16. 16. • Avoid DES, RC4, MD5, 3DES key length < 128, export ciphers • Prefer AES, GCM, SHA2, TLSv1.2, OpenSSL >= 1.0.1p / 1.0.2d • Not all permutations of these are supported (see: cipher suites) • Sometimes you are dependent on vendor support (e.g. hardware load balancers) • Some servers deliberately configured with weak ciphers to support old browsers (IE6 still in use) • Cert expiration is just one reason to replace them (other reasons: use of SHA1, weak key sizes, cert revocation, CA compromises, etc) www.rackspace.com 16 Server configuration
  17. 17. Example nginx configuration ssl_protocols TLSv1.2 TLSv1.1 TLSv1; ssl_ciphers ECDHE-RSA-AES256-GCM-SHA384:ECDHE-RSA-AES128-GCM- SHA256:DHE-RSA-AES256-GCM-SHA384:DHE-RSA-AES128-GCM- SHA256:ECDHE-RSA-AES256-SHA384:ECDHE-RSA-AES256-SHA:DHE-RSA- AES256-SHA; ssl_prefer_server_ciphers on; Example Apache configuration SSLProtocol All -SSLv2 -SSLv3 SSLCipherSuite HIGH:!aNULL:!MD5 SSLHonorCipherOrder on More in-depth examples can be found on https://cipherli.st/ www.rackspace.com 17 Configuration examples
  18. 18. • Certificate ordered/installed has too short a key (< 1024 bits) • Full certificate chain (CA bundle) not installed • Preferred cipher not set correctly • ‘Honor cipher order’ feature not turned on • SSL engine/library outdated • Server not sufficiently protected (so private key is not protected) • Servers in load balance group configured inconsistently www.rackspace.com 18 Other server configuration issues
  19. 19. • Protects past conversations even if server private key is compromised • Uses ephemeral keys in key agreement protocols • ECDHE_ECDSA, DHE_RSA www.rackspace.com 19 PFS (Perfect Forward Secrecy)
  20. 20. • Server configuration to only accept secure connections for this site • Server initially sends Strict-Transport-Security header to browser • Browser makes a note that site should only be accessed with HTTPS • If an attempt is made to connect to port 80, force user to reconnect via HTTPS (port 443 by default) • Particularly useful if sites mix secure and unsecure resources www.rackspace.com 20 STS / HSTS
  21. 21. 21www.rackspace.com Vulnerabilities
  22. 22. • Heartbleed (leaks random memory in plain text. Fixed in OpenSSL 1.0.1g) • Logjam (force export ciphers) / WeakDH (weak/reused Diffie-Hellman params) • BEAST (browser issue but can be mitigated server side. TLSv1 and earlier) • CRIME (TLSv1 compression) • FREAK (export ciphers) • POODLE (affects SSLv3) www.rackspace.com 22 Some recent vulnerabilities
  23. 23. • Problem: MITM can force client and server to agree to use a lower protocol version than what they actually support • Note: The above is possible because SSL/TLS handshake is in cleartext (session key has not been agreed to yet) • Solution: Browser include a dummy cipher to tell the server to check whether its highest protocol version is greater than ClientHello’s. If so, abort communication. • Fake ciphers (x00FF) – EMPTY-RENEGOTIATION-INFO-SCSV – TLS_FALLBACK_SCSV * Signaling Cipher Suite Value www.rackspace.com 23 TLS downgrade attack protection (SCSV*)
  24. 24. • Ciphers allowed by the US Government for the export market • Devised in the 1990’s. Laws restricting encryption export are no longer in force. • TLS 1.2 no longer includes them • Export ciphers use short keys (40-56 bit), making them insecure • Identified by the presence of EXP or EXPORT in their name www.rackspace.com 24 Export ciphers
  25. 25. 25www.rackspace.com
  26. 26. • Just because an endpoint is acceptable today does not mean it will remain so tomorrow since: –Certificates expire –Servers are reconfigured –New vulnerabilities are uncovered –Increasing computing power can make old standards/assumptions obsolete (e.g. SHA1) • This means you need to be constantly monitoring your endpoints www.rackspace.com 26 In summary
  27. 27. www.rackspace.com 27 Constantly?!
  28. 28. 28www.rackspace.com How to keep up?!
  29. 29. • OpenSSL's "s_client" is useful for debugging SSL. On most Linux/UNIX systems, you can call it like so: openssl s_client [-debug] –host host.com –port 443 • The "-debug" flag will give you more information about the actual connection, showing a hex dump of the handshake and negotiation process • Doesn't tell you much about vulnerabilities, but gives you the information you need if you already know what you're looking for www.rackspace.com 29 OpenSSL's s_client
  30. 30. From the testssl.sh site: "testssl.sh is a free command line tool which checks a server's service on any port for the support of TLS/SSL ciphers, protocols as well as recent cryptographic flaws and more." www.rackspace.com 30 testssl.sh
  31. 31. • Reports SSL/TLS issues such as: – SSL/TLS version – Weak protocols, ciphers and hashes – Known vulnerabilities • Uses an easy to understand letter rating system • Scoring is calculated by assigning weights to: – Protocol support (30%) – Key exchange support (30%) – Cipher strength (40%) • Can be accessed through API – Official API client here: https://github.com/ssllabs/ssllabs-scan www.rackspace.com 31 Qualys SSL Labs
  32. 32. Score Meaning A+ Domains with no warnings and use HSTS and TLS_FALLBACK_SCSV A Domains with 2048 bit keys, at least TLS 1.2 support and no warnings A- Domains with 2048 bit keys, at least TLS 1.2 support but with some warnings B Uses SSL 3.0, RC4, missing intermediate certificates, vulnerable to BEAST or CRIME, NS >= 65 C Domain is vulnerable to POODLE, NS >= 50 D Numeric Score >= 35 E Numeric Score >= 20 M Domain and cert host mismatch T Certificate is not trusted F Uses MD5, keys with length < 1024, or SSLv3 is the strongest protocol supported www.rackspace.com 32 Qualys letter rating system
  33. 33. 33www.rackspace.com You want an A+, right?
  34. 34. • https://cipherli.st • Collection of good configurations for TLS/SSL, covering several different servers (Apache, nginx, HAProxy, Postfix, OpenSSH …) • Useful for making recommendations to product teams for software you might not have configured before • Simple copy-and-paste format takes headaches out of implementers making decisions about certain ciphers or other settings (though you should vet these configurations based on what clients you want/need to support!) www.rackspace.com 34 Cipherli.st
  35. 35. • Hosts several endpoints with broken SSL configurations • Great resource for vetting SSL verification code / test scripts • Examples: –https://expired.badssl.com/ –https://self-signed.badssl.com/ • Many, many more! www.rackspace.com 35 badssl.com
  36. 36. www.rackspace.com 36 Wanna manage all those endpoints manually?
  37. 37. www.rackspace.com 37 One possible solution: TLSManager
  38. 38. • Automatically scans daily all endpoints in its database • Uses Qualys Labs SSL tool (https://www.ssllabs.com/ssltest) • Reports SSL vulnerabilities • Proactively warns of any certificates about to expire • Emails reports to interested parties • Keeps a history of the results www.rackspace.com 38 Features
  39. 39. 39www.rackspace.com DEMO TIME
  40. 40. 40www.rackspace.com
  41. 41. • On Github: https://github.com/rackerlabs/TLSManager OR http://bit.ly/1MUQiss • License: Apache 2.0 • Pull requests most welcome! www.rackspace.com 41 Go get it!
  42. 42. 42www.rackspace.com Current Events
  43. 43. www.rackspace.com 43 Google + BoringSSL
  44. 44. www.rackspace.com 44 Let's Encrypt
  45. 45. www.rackspace.com 45 SHA-1 IS TOTES BROKEN! SAVE YOURSELF!
  46. 46. www.rackspace.com 46 SHA-1 IS TOTES BROKEN! SAVE YOURSELF!
  47. 47. www.rackspace.com 47 Diffie-Hellman APOCALYPSE!1!!
  48. 48. • SSL/TLS management is more involved than it looks at first • Lots of moving parts • A constantly changing landscape: a server rated A+ today can be downgraded tomorrow if: – Certs expire – New cipher vulnerabilities are uncovered – Bugs in SSL/TLS libraries are reported – Server is misconfigured – Cert or CA compromise • It's helpful to monitor SSL endpoints in an automated way to keep from missing any issues www.rackspace.com 48 Closing thoughts
  49. 49. www.rackspace.com 49 Questions? Charles Neill Twitter: @ccneill Github: cneill Email: cneill@inventropy.us Henry Yamauchi Email: henry.yamauchi@rackspace.com
  50. 50. • Group that focuses on the security of one of the largest open source projects in the world! • IRC channel: #openstack-security on Freenode • Weekly meetings: #openstack-meeting-alt @ 1700 UTC Thursdays • Mailing list: openstack-dev ML with [Security] tag www.rackspace.com 50 OpenStack Security Project
  51. 51. THANK YOU RACKSPACE® | 1 FANATICAL PLACE, CITY OF WINDCREST | SAN ANTONIO, TX 78218 US SALES: 1-800-961-2888 | US SUPPORT: 1-800-961-4454 | WWW.RACKSPACE.COM © RACKSPACE LTD. | RACKSPACE® AND FANATICAL SUPPORT® ARE SERVICE MARKS OF RACKSPACE US, INC. REGISTERED IN THE UNITED S TATES AND OTHER COUNTRIES. | WWW.RACKSPACE.COM

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