unsafe ssl webinar

Detecting and addressing unsafe SSL configurations

Jonathan Trull, Wolfgang Kandek, Ivan Ristic!SSL Labs/Qualys

March 26, 2015

CISO’s View of SSL/TLS

•  Key Component for Doing Business Online •  Administra8ve burden as organiza8ons grow in size

•  Compliance and Regulatory Requirements •  PCI •  FedRAMP •  HIPAA •  Graham-‐Leach-‐Bliley Act

•  Reputa8on / Ensuring Trust

PCI-DSS Deep Dive •  Use strong cryptography and security protocols

to safeguard cardholder data during transmission over open, public networks.

•  PCI SSC Bulletin dated 13 February 2015

•  No version of SSL meets PCI SSC’s definition of “strong cryptography.”

•  PCI Data Security Standard and the Payment Application Data Security Standard are being updated to reflect this change.

BitSight Third-Party Due Diligence

Events •  Botnet Infections •  Spam Propagation •  Malware Servers •  Unsolicited Comm. •  Potentially Exploited

Diligence •  SPF Domains •  DKIM Records •  TLS/SSL Certificates •  DNSSEC Records •  Data Breaches

SSL History •  Secure communica8on on the Internet

•  E-‐commerce •  Secure Sockets Layer – Netscape – 1994

•  SSL v1,v2 – SSLv3 •  TLS 1.2

•  Typically hWps rather than hWp in your browser

SSL History

SSL History •  Secure communica8on on the Internet

•  E-‐commerce •  Secure Sockets Layer – Netscape – 1994

•  SSL v1,v2 – SSLv3 •  TLS 1.2

•  Typically hWps rather than hWp in your browser •  Other less visibly uses: VPN, Mail, FTP…

SSL •  Privacy – Encryp8on

•  Ciphers: RC4, AES •  Integrity – Hashing

•  Hash-‐func8ons: SHA1, SHA-‐256 •  Authen8ca8on – Cer8ficates

Qualys SSL Labs

https://www.ssllabs.com/

Qualys SSL Labs Server Test

Server Rating

SSL Vulnerabilities •  Protocol vs Implementa8on •  Implementa8ons: OpenSSL, Schannel, GnuTLS, PolarSSL,

LibreSSL, NSS, BSAFE, Secure Transport

•  BREACH, CRIME – 2012

•  Heartbleed – April 2014

•  HTTPS request to a website •  https://hbdemo.kandek.com •  Site with registration, login, sessions •  Data: username, password, email •  Ubuntu 12.04, Apache, OpenSSL, MySQL •  Data gets written to database •  But stays in memory as well

SSL: Heartbleed

Heartbleed - details

•  Heartbeat extension is enabled: good for performance as it keeps the session alive

•  The Heartbeat extension has a programming flaw that allows us to receive more bytes than we sent: •  Regular: sent “abc”, length 3, received “abc” •  Exploit: send “abc” length 64, received “abc” plus registration

data •  Size upto 64 KB, not logged, can be repeated freely

SSL

•  HTTPS request to a website •  https://hbdemo.kandek.com •  Simple site with registration, login, sessions

SSL

Heartbleed – What can leak

•  Session key cookies •  PHPSESSIONID = 0xFFA34E2DE7E1

•  Userdata, including passwords •  Wait - Shouldn’t they be hashed? •  Passwords are typically not hashed on client, but on server

•  Private key for certificate •  Allows for decryption of all traffic, future and past

Heartbleed – Leak demo

•  Session key cookies •  PHPSESSIONID = 0xFFA34E2DE7E1

•  Userdata, including passwords •  Wait - Shouldn’t they be hashed? •  Passwords are typically not hashed on client, but on

server •  Private key for certificate

•  Allows for decryption of all traffic, future and past

SSL

•  HTTPS request to a website •  https://ubudc.kandek.com •  Simple site with registration, login •  Data: Username, password, email •  Ubuntu 12.04, Apache, OpenSSL, MySQL •  Data gets written to database •  But stays in memory as well

SSL Vulnerabilities •  Protocol vs Implementa8on •  Implementa8ons: OpenSSL, Schannel, GnuTLS, PolarSSL,

LibreSSL, NSS, BSAFE, Secure Transport

•  BREACH, CRIME – 2012

•  Heartbleed – April 2014

•  POODLE – October 2014

•  FREAK – February 2015

•  OpenSSL – DoS in March 2015

SSL - Making the Grade


•  Instruc8ons for Apache, Tomcat, IIS and nginx

Qualys SSL Labs Server Test

SSL Labs API •  SSL Labs is a web applica8on, designed for interac8ve use •  API has been o`en requested

•  March 2015 SSL Labs release: API •  HTTP/JSON •  https://api.ssllabs.com/api/v2/analyze?host=www.ssllabs.com •  Docs at: hWps://github.com/ssllabs/ssllabs-‐scan

•  Sample Command line tool: ssllabs-‐scan •  Go Implementa8on: hWps://github.com/ssllabs/ssllabs-‐scan/

SSL Labs API

SSL Labs API •  SSL Labs is a web applica8on, designed for interac8ve use •  API has been o`en requested

•  March 2015 SSL Labs release: API •  HTTP/JSON •  https://api.ssllabs.com/api/v2/analyze?host=www.ssllabs.com •  Docs at: hWps://github.com/ssllabs/ssllabs-‐scan

•  Sample Command line tool: ssllabs-‐scan •  Go Implementa8on: hWps://github.com/ssllabs/ssllabs-‐scan/

SSL Statistics - Pulse

SSL Clientside

SSL Labs Roadmap

•  HSTS detec8on •  Mixed Content detec8on •  MITM aWack detec8on •  IPv6 •  Beyond HTTP

SSL – Other issues – Superfish •  Lenovo preinstalls Superfish so`ware on consumer laptops •  Superfish decrypts SSL connec8ons on the machines to be

able to read the SSL content and serve ads in the SSL content stream

•  To do this transparently it installs a new root cer8ficate on the local machine and intercepts all SSL traffic resigning the site with its own cer8ficate

•  Superfish objec8ve: MITM for ad revenue, i.e modify the web content on the fly, replace and inject ads with “beWer” ads, not an “aWack”

Example – Superfish installed

Lock indicates valid SSL connection

Strong encryption

Certificate issued by Superfish – not Verisign

Example – the real Qualys

EV certificate (green)

Superfished SSL Connections

SSL – Other issues – CA problems •  Browsers trust a large set of CAs to correctly emit cer8ficates •  Some8mes this goes wrong


•  Recent Google CNNIC, similar last year in France, discovered through cer8ficate pinning


•  Recent Google CNNIC, similar last year in France, discovered through cer8ficate pinning

•  Domain ownership by e-‐mail is weak

Helpful Resources SSL/TLS Deployment Best Practices -

https://www.ssllabs.com/downloads/SSL_TLS_Deployment_Best_Practices.pdf

SSL Server Rating Guide – https://www.ssllabs.com/downloads/SSL_Server_Rating_Guide.pdf

SSL Labs API Guide - https://www.ssllabs.com/projects/ssllabs-apis/index.html

Bulletproof SSL and TLS - Ivan Ristic https://www.feistyduck.com/books/bulletproof-ssl-and-tls/

Thank You Jonathan Trull

[email protected]

Wolfgang Kandek [email protected]

@wkandek

Ivan Ris8c @ivanris8c

hWp://www.qualys.com

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