SlideShare a Scribd company logo
The Certificate Farce
Boise BSides 11-21-2015
SANS Master’s Student
Sandra (Sandy) Dunn
HP Cybersecurity
subzer0girl@gmail.com
Twitter @subzer0girl
Thank you for data & research support !
Jim Lairmore, HP Inc.
Kevin Bocek, Venafi
Dan DeSantis, Venafi
• You live where multiple organizations can issues driver license ID’s
• Some of those organizations include ones that the governments have control and
are known to be untrustworthy
• Some of these organizations don’t have great processes and accidently issue IDs
to people they shouldn’t (whoops)
• The ID’s are the only way you know which business or individuals you can trust
with your private and financial data
• There are criminals actively trying to trick you to get your data
• When you ask for an ID there is a security officer that helps you check the ID.
He warns you if the driver’s license is out of date, if the license was written
with bad ink, or if the name on the license doesn’t match the name the person
or business told you. You ignore him a lot… You used to try to listen, but you
can’t really understand what he is telling you and he used to say “it’s not
safe it’s not safe” and it was safe the driver license was just out of date.
The people forgot to get a new one.
• When someone has their ID stolen or bad guys steal people’s stuff after showing
them their driver’s license then their ID is revoked.
• To see if a person ID was revoked you have to ask the organization for all the
driver’s licenses that they have revoked. They send you back a book the size
of set of encyclopedias and that can take several days. Sometimes it’s hard to
know where to ask for the books because they change the address of where to go
get them. It got too hard you mostly don’t ask any more.
How confident are you that you can trust the
ID’s that people use to prove their identity?
• These driver’s licenses perform another very important task for you. They help
you know what food is safe to eat because unfortunately there are people
actively and aggressively trying to poison you.
• When you get food there is signature on the food that is signed by the people
who made it. You determine if the food is safe based on whether you trust who
made the food.
• The people who want to poison you know that you trust the signature and will
eat anything if it is signed by someone you trust.
• They actively try to steal the special pens used to make the signatures you
trust. Some businesses know this and protect the pen and lock them up. Some
businesses just leave the pen laying around.
• The truth is the people trying to poison you don’t really need to work very
hard to steal pens for the special signatures.
• The people who sell the special pens that make the signatures really need to
make money and they will really sell them to anyone without asking too many
questions.
How confident are you that
you won’t get poisoned
Alexander Litvinenko
November 1 2006, Litvinenko suddenly fell ill and was hospitalized
from poisoning by radioactive polonium-210. He died November 23.
https://en.wikipedia.org/wiki/Alexander_Litvinenko
Andrey Lugovo
Do free TLS certificate make the internet
more secure?
https://letsencrypt.org/
http://www.infoworld.com/article/2984243/security/the-perils-of-free-digital-certificates.html#tk.ifw-infsb
At the end of this presentation
Know where to
find data that
supports how
often
certificate
trust is broken
Less blind
trust in code
signing
Hold people and
sites
accountable for
out of date /
self signed
certificates
Align with the
urgency to
manage
certificates in
your
environment
Know about
some tools
• TLS 1.3 RFC expected in April 2016
• SHA1 no longer supported January 1, 2016
• NIST December 2015
• Google December 2015
• Microsoft June 2016
• Mozilla July 2016
Keynote: Alex Stamos
The Moral Imperatives and Challenges for Modern Application Security
https://www.youtube.com/watch?v=_xVoBA1f4gY
Coming TLS changes
Common TLS Certificates Trust Anchors
• Website
• Code Signing Certificates
• S/MIME email encryption
• Digital ID / User Identity
• SSH
• RDP
• Business to Business Applications
• VOIP
• VPN
• IoT
Recent Code Signing Key Compromise News
10.28.15 Google to Symantec – “You have until June to fix this or we will
flag Symantec issued certificates as vulnerable”
We issued 23
test
certificates
That seems
low, we don’t
believe you
Ok, your right
it’s 2,458
Certificates
http://arstechnica.com/security/2015/10/still-fuming-over-https-mishap-google-gives-symantec-an-offer-it-cant-refuse/
http://techcrunch.com/2015/11/12/all-mac-store-apps-stopped-working-due-to-expired-security-certificate/#.y37x7x:xhzD
More Certificate Pain
• Komodia TLS intercept libraries
• MITM HTTPS traffic
• EFF Recommends reinstalling a
fresh OS
https://www.eff.org/deeplinks/2015/02/dear-software-vendors-please-stop-trying-intercept-your-customers-encrypted
Considering that Lenovo implemented
this intentionally and the potential
damage, was this a criminal act ?
Netcraft research indicates Certificate Authorities
aren’t flagging domains with names that are similar
to common, high traffic sites.
Universal SSL certificates (free CloudFlare
certificate) accounted for 40 percent of
certificates used by phishing sites.
http://www.infoworld.com/article/2992605/security/phishing-sites-exploit-trust-in-valid-ssl-certificates.html
CRL (Certificate Revocation List ) • blacklist of revoked
certificates
• Often hard coded in the url
• Often disabled because of
the length of time to check
OCSP (Online Certificate Status Protocol) • Improvement over CRL lists
but the soft fail defeats
the purpose
OCSP Stapling best option • Requires implementation by
Web Server Administrator to
implement
• SSLLabs.com OCSP Stapling
will become a factor in
your grade
TLS Certificate Revocation
And the bad guys know it doesn’t really work....
8 % of the certificates being
served had been revoked
SANS Internet Storm Center
https://isc.sans.edu/crls.html?token=e01d79423885ad9aac53ab92eb75274c116b548e&startdate=2014-10-04&enddate=2015-11-03&submit=Update
Presentation2 certificate farce
OCSP Certificate
Pinning
OCSP Stapling requires the website administrators to
enable it on their web server
Certificate
Transparency
Add a layer of visibility to domain owners for CA issued
TLS certificates. an open auditing and monitoring system
that lets any domain owner or CA determine whether
certificates have been mistakenly or maliciously issued.
TACK Dynamic certificate framework. TACK requires protocol
changes for both the server and the client side of any SSL
transaction which has been met with a cold reception.
Convergence Instead of hard coded CA’s. Convergence configures a
dynamic set of Notaries. No incentive for the notary
investment
Sovereign Keys Addressed issues like the ineffectiveness of browser
certificate warnings. Ended up just really replacing one
remote authority with another.
DANE DNS Authentication of Named Entities a proposal based on
DNSSEC to eventually replace the CA system. It is based on
the idea of using the DNS hierarchy to issue SSL certs the
same way that domains are managed and resolved - with few
root keys & individual organizations in charge. The
challenge is that countries that have little trust would
be required to trust the reliability of the DANE entry.
TLS Tools
OWASP OWASP Cheat Sheets
OWASP Testing tools
OWASP.org
TLSSLed TLSSLed is Linux shell script to
evaluate the security of target
Kali Linux
O-Saft OWASP SSL advanced forensic tool /
OWASP SSL audit for testers
https://www.owasp.org/index.php/O-Saft
ssldump – An SSL/TLS network
protocol analyzer
It identifies TCP connections on the
chosen network interface and attempts
to interpret them as SSL/TLS traffic.
When it identifies SSL/TLS traffic, it
decodes the records and displays them
in a textual form to stdout. If
provided with the appropriate keying
material, it will also decrypt the
connections and display the
application data traffic.
http://ssldump.sourceforge.net/
SSLyze check for web SSL/TLS and also
STARTTLS for smtp, xmpp, pop3, ftp,
imap, ldap and rdp
https://github.com/nabla-c0d3/sslyze
SSL Server Test Provides a grade of a
sites TLS implementation
https://www.ssllabs.com/ssltest/
SSL Client Test Client TLS information https://www.ssllabs.com/ssltest/viewMy
Client.html
Prevention Ideal, Detection a Must !
But you won’t see this in your logs……
Censys Shodan Alexa
Netcraft Google
Hacks
Internet
Archives
205,477
Censys
https://www.censys.io/
This doesn’t look good …
https://sonar.labs.rapid7.com/
Project Sonar
Sonar collects SSL Certificates, Web Server responses, DNS
records, and responses from common UDP services. We use this
data to identify large-scale misconfigurations and
vulnerabilities in consumer, enterprise, and critical
infrastructure systems.
All Sonar data is provided to the public free of charge in
cooperation with the University of Michigan. You can find the
data at Scans.IO.
SSL/TLS Filters
Cert Version
Cert Bits
Cert Issuer
Cert Subject / Cert Name
Check for known issues (Heartbleed)
Cipher Bits / Protocol
Grab cert for all services
27
Searches and indexes by responses to queries
https://shodanio.wordpress.com/2014/06/16/kicking-the-shodan-api-up-a-notch/
Blue+Coat+PacketShaper
Presentation2 certificate farce
• What certificates are present on a given IP?
• Which client IPs access a given service?
Flying Pig – TLS Knowledge Base
https://www.circl.lu/services/passive-ssl/
http://blog.squarelemon.com/
DerbyCon TLS Fingerprinting
Lee Brotherston @synackpse
• Recognizing a TLS Fingerprint is possible by
Capturing client TLS initial hello packets
• Recognize SuperFish, PrivDog, and GeniusBox
clients in network traffic
“Using TLS fingerprinting we can quickly and passively
determine which client is being used, and apply strategies
from both the attacker and defender perspectives. These
strategies allow us to achieve smarter defending and
stealthier attacking” Lee Brotherston
http://www.infoworld.com/article/2992605/security/phishing-sites-exploit-trust-in-valid-ssl-certificates.html
Netcraft TLS Certificate Services
Deceptive
Domain Score
analyzes the likelihood that a domain name
will be used for fraudulent activities.
Phishing Alert
Service
sends an alert if your site / certificate is
used for a phishing scam
Urgent need to proactively
manage TLS Certificate
inside and outside your
firewall
Think about
code signing
trust
Hold people and sites
accountable for out of date
/ self signed certificates
Start now
it’s going to
get worse
Summary
OWASP https://owasp.org Cheat Sheets Key Pinning, TLS testing,
CA Security Council https://casecurity.org/ is a multi-vendor industry advocacy group created
to conduct research, promote Internet security
standards and educate the public on Internet
security issues.
CA Browser (CAB) forum, which is a group that
includes both CAs and web browser vendors.
https://cabforum.org/ Voluntary consortium of certification authorities,
vendors of Internet browser software, operating
systems, and other PKI-enabled applications
industry guidelines governing the issuance and
management of X.509 v.3 digital certificates.
Online Trust Alliance https://otalliance.org/resources/SSL/CABestPractice
s.html
European Telecommunications Standards Institute
(ETSI)
www.etsi.org independent, not-for-profit, standardization
organization in the telecommunications industry) in
Europe
W3C http://www.w3.org/2001/tag/doc/web-https TAG’s position on securing the Web through the use
of cryptography, identifies some of the associated
issues, and recommends further work to aid in its
use.
Its primary audience is W3C participants
Title Link
PKI Trust Models: Whom Do You Trust https://www.sans.org/reading-room/whitepapers/vpns/pki-trust-models-
trust-36112
Digital Certificate Revocation https://www.sans.org/reading-room/whitepapers/certificates/digital-
certificate-revocation-35292
Building and Managing a PKI Solution for Small and Medium Size Business https://www.sans.org/reading-room/whitepapers/certificates/building-
managing-pki-solution-small-medium-size-business-34445
SSl/TLS: What’s Under the Hood https://www.sans.org/reading-room/whitepapers/authentication/ssl-tls-
hood-34297
Windows Enforcement of Authenticode Code Signing and Timestamping http://social.technet.microsoft.com/wiki/contents/articles/32288.windo
ws-enforcement-of-authenticode-code-signing-and-timestamping.aspx
The Scary and Terrible Code Signing Problem You Don’t Know You Have https://www.sans.org/reading-room/whitepapers/certificates/scary-
terrible-code-signing-problem-don-039-t-36382
The Business Case For TLS Certificate Enterprise Key Management https://www.sans.org/reading-room/whitepapers/critical/business-
case-tls-certificate-enterprise-key-management-web-site-certificates-
wrangling-36392
http://wiki.cacert.org/Risk/History
History of Certificate Risks & Threats
More Fear Uncertainty and Doubt
http://www.cs.utexas.edu/~shmat/shmat_ccs12.pdf
We’ve focused on browser based TLS,
there are many other applications
that rely on TLS libraries and have
validation challenges.
More Work To do
https://www.blackhat.com/docs/us-15/materials/us-15-Gavrichenkov-Breaking-HTTPS-With-BGP-Hijacking.pdf
BGP Hijacking
The problem is: the
encryption is backed
by SSL/TLS PKI
Sniffly
Sniffly is an attack that abuses HTTP
Strict Transport Security and Content
Security Policy to allow arbitrary
websites to sniff a user's browsing
history. It has been tested in Firefox
and Chrome
https://github.com/diracdeltas/sniffly
Highly classified decryption program run by the NSA
The British signals intelligence agency GCHQ has a
similar program codenamed Edgehill.
http://www.spiegel.de/media/media-35531.pdf
Bullrun

More Related Content

PDF
Symantec Infogrphic - SSL Certificate Management
PDF
Business Critical SSL Certificate Management - Infographic
PDF
Ponemon - Cost of Failed Trust: Threats and Attacks
PDF
Four Must Know Certificate and Key Management Threats That Can Bring Down You...
PDF
Young Gun - Drew Evans-3
PDF
Five Must Haves to Prevent Encryption Disasters
PDF
SANS 20 Critical Security Control 17 Requirements for SSL/TLS Security and Ma...
PPTX
Certificate authorities under attack :A
Symantec Infogrphic - SSL Certificate Management
Business Critical SSL Certificate Management - Infographic
Ponemon - Cost of Failed Trust: Threats and Attacks
Four Must Know Certificate and Key Management Threats That Can Bring Down You...
Young Gun - Drew Evans-3
Five Must Haves to Prevent Encryption Disasters
SANS 20 Critical Security Control 17 Requirements for SSL/TLS Security and Ma...
Certificate authorities under attack :A

Viewers also liked (16)

PDF
PPTX
Kent King - PKI: Do You Know Your Exposure?
DOC
HẠ TẦNG KHÓA CÔNG KHAI(PKI)
PPTX
Tutorial membuat Public Key Infrastructure
PPTX
Securing your Windows Network with the Microsoft Security Baselines
PPTX
Implementing a Secure and Effective PKI on Windows Server 2012 R2
PDF
B.Noviansyah - “National Public Key Infrastructure: Friend or Foe?"
PDF
Switch to SHA-2 SSL - A Step-by-Step Migration Guide
PPT
Marco Casassa Mont: Pki overview
PPT
Introduction To PKI Technology
PPT
PKI and Applications
PPTX
Pki for dummies
PDF
F5 TLS & SSL Practices
PDF
PKI Industry growth in Bangladesh
Kent King - PKI: Do You Know Your Exposure?
HẠ TẦNG KHÓA CÔNG KHAI(PKI)
Tutorial membuat Public Key Infrastructure
Securing your Windows Network with the Microsoft Security Baselines
Implementing a Secure and Effective PKI on Windows Server 2012 R2
B.Noviansyah - “National Public Key Infrastructure: Friend or Foe?"
Switch to SHA-2 SSL - A Step-by-Step Migration Guide
Marco Casassa Mont: Pki overview
Introduction To PKI Technology
PKI and Applications
Pki for dummies
F5 TLS & SSL Practices
PKI Industry growth in Bangladesh
Ad

Similar to Presentation2 certificate farce (20)

PDF
RIPE 84: Revocation
PDF
Is web security part of your annual security audit
PDF
SSL: Past, Present and Future
PDF
SSL: Past, Present and Future
PDF
Keynectis SSL Certificate - Expert Advice
PDF
Geoff Huston's presentation on DANE (Keys in the DNS) at the New Zealand Inte...
PDF
Trust and Security, presented by Geoff Huston
PDF
Understanding The World Of SSL Certificates.pdf
PPTX
Symantec SSL Explained
PPTX
Масштабируя TLS
PPTX
Масштабируя TLS / Артём Гавриченков (Qrator Labs)
PDF
All About SSL/TLS
PPTX
Certificate pinning in android applications
PDF
Reducing Fraud with the Right SSL Certificate in E-Commerce
PPTX
Believe It Or Not SSL Attacks
PPTX
Self-Signed SSL Versus Trusted CA Signed SSL Certificate
PDF
An Introduction to DANE - Securing TLS using DNSSEC
PDF
DEF CON 23 - BRENT - white hacking web apps wp
PPTX
Web application security part 02
PPTX
HTTP vs HTTPS, Do You Really Need HTTPS?
RIPE 84: Revocation
Is web security part of your annual security audit
SSL: Past, Present and Future
SSL: Past, Present and Future
Keynectis SSL Certificate - Expert Advice
Geoff Huston's presentation on DANE (Keys in the DNS) at the New Zealand Inte...
Trust and Security, presented by Geoff Huston
Understanding The World Of SSL Certificates.pdf
Symantec SSL Explained
Масштабируя TLS
Масштабируя TLS / Артём Гавриченков (Qrator Labs)
All About SSL/TLS
Certificate pinning in android applications
Reducing Fraud with the Right SSL Certificate in E-Commerce
Believe It Or Not SSL Attacks
Self-Signed SSL Versus Trusted CA Signed SSL Certificate
An Introduction to DANE - Securing TLS using DNSSEC
DEF CON 23 - BRENT - white hacking web apps wp
Web application security part 02
HTTP vs HTTPS, Do You Really Need HTTPS?
Ad

More from Sandra (Sandy) Dunn (7)

PDF
Osint part 1_personal_privacy
PDF
Data goverance two_8.2.18 - copy
PDF
Your're Special (But Not That Special)
PDF
Bsu skills and_careers_in_cybersecurity
PDF
Step by-step-guide risk-security-dunn_firth_v.1.8
PDF
Banning Whining, Avoiding Cyber Wolves, and Creating Warrior
DOC
Transformational Leadership: Inspiring Motivation Utilizing Advances in Posit...
Osint part 1_personal_privacy
Data goverance two_8.2.18 - copy
Your're Special (But Not That Special)
Bsu skills and_careers_in_cybersecurity
Step by-step-guide risk-security-dunn_firth_v.1.8
Banning Whining, Avoiding Cyber Wolves, and Creating Warrior
Transformational Leadership: Inspiring Motivation Utilizing Advances in Posit...

Recently uploaded (20)

PPTX
KOM of Painting work and Equipment Insulation REV00 update 25-dec.pptx
PPTX
Effective Security Operations Center (SOC) A Modern, Strategic, and Threat-In...
PDF
TokAI - TikTok AI Agent : The First AI Application That Analyzes 10,000+ Vira...
PDF
Building Integrated photovoltaic BIPV_UPV.pdf
PDF
Machine learning based COVID-19 study performance prediction
PDF
Encapsulation theory and applications.pdf
PPTX
MYSQL Presentation for SQL database connectivity
PPTX
Detection-First SIEM: Rule Types, Dashboards, and Threat-Informed Strategy
PPTX
20250228 LYD VKU AI Blended-Learning.pptx
PPT
“AI and Expert System Decision Support & Business Intelligence Systems”
PPTX
A Presentation on Artificial Intelligence
PDF
Spectral efficient network and resource selection model in 5G networks
PDF
Modernizing your data center with Dell and AMD
PPT
Teaching material agriculture food technology
PDF
Reach Out and Touch Someone: Haptics and Empathic Computing
PDF
NewMind AI Weekly Chronicles - August'25 Week I
PDF
Unlocking AI with Model Context Protocol (MCP)
PDF
Diabetes mellitus diagnosis method based random forest with bat algorithm
PPTX
PA Analog/Digital System: The Backbone of Modern Surveillance and Communication
PDF
Build a system with the filesystem maintained by OSTree @ COSCUP 2025
KOM of Painting work and Equipment Insulation REV00 update 25-dec.pptx
Effective Security Operations Center (SOC) A Modern, Strategic, and Threat-In...
TokAI - TikTok AI Agent : The First AI Application That Analyzes 10,000+ Vira...
Building Integrated photovoltaic BIPV_UPV.pdf
Machine learning based COVID-19 study performance prediction
Encapsulation theory and applications.pdf
MYSQL Presentation for SQL database connectivity
Detection-First SIEM: Rule Types, Dashboards, and Threat-Informed Strategy
20250228 LYD VKU AI Blended-Learning.pptx
“AI and Expert System Decision Support & Business Intelligence Systems”
A Presentation on Artificial Intelligence
Spectral efficient network and resource selection model in 5G networks
Modernizing your data center with Dell and AMD
Teaching material agriculture food technology
Reach Out and Touch Someone: Haptics and Empathic Computing
NewMind AI Weekly Chronicles - August'25 Week I
Unlocking AI with Model Context Protocol (MCP)
Diabetes mellitus diagnosis method based random forest with bat algorithm
PA Analog/Digital System: The Backbone of Modern Surveillance and Communication
Build a system with the filesystem maintained by OSTree @ COSCUP 2025

Presentation2 certificate farce

  • 1. The Certificate Farce Boise BSides 11-21-2015
  • 2. SANS Master’s Student Sandra (Sandy) Dunn HP Cybersecurity subzer0girl@gmail.com Twitter @subzer0girl Thank you for data & research support ! Jim Lairmore, HP Inc. Kevin Bocek, Venafi Dan DeSantis, Venafi
  • 3. • You live where multiple organizations can issues driver license ID’s • Some of those organizations include ones that the governments have control and are known to be untrustworthy • Some of these organizations don’t have great processes and accidently issue IDs to people they shouldn’t (whoops) • The ID’s are the only way you know which business or individuals you can trust with your private and financial data • There are criminals actively trying to trick you to get your data • When you ask for an ID there is a security officer that helps you check the ID. He warns you if the driver’s license is out of date, if the license was written with bad ink, or if the name on the license doesn’t match the name the person or business told you. You ignore him a lot… You used to try to listen, but you can’t really understand what he is telling you and he used to say “it’s not safe it’s not safe” and it was safe the driver license was just out of date. The people forgot to get a new one. • When someone has their ID stolen or bad guys steal people’s stuff after showing them their driver’s license then their ID is revoked. • To see if a person ID was revoked you have to ask the organization for all the driver’s licenses that they have revoked. They send you back a book the size of set of encyclopedias and that can take several days. Sometimes it’s hard to know where to ask for the books because they change the address of where to go get them. It got too hard you mostly don’t ask any more.
  • 4. How confident are you that you can trust the ID’s that people use to prove their identity?
  • 5. • These driver’s licenses perform another very important task for you. They help you know what food is safe to eat because unfortunately there are people actively and aggressively trying to poison you. • When you get food there is signature on the food that is signed by the people who made it. You determine if the food is safe based on whether you trust who made the food. • The people who want to poison you know that you trust the signature and will eat anything if it is signed by someone you trust. • They actively try to steal the special pens used to make the signatures you trust. Some businesses know this and protect the pen and lock them up. Some businesses just leave the pen laying around. • The truth is the people trying to poison you don’t really need to work very hard to steal pens for the special signatures. • The people who sell the special pens that make the signatures really need to make money and they will really sell them to anyone without asking too many questions.
  • 6. How confident are you that you won’t get poisoned Alexander Litvinenko November 1 2006, Litvinenko suddenly fell ill and was hospitalized from poisoning by radioactive polonium-210. He died November 23. https://en.wikipedia.org/wiki/Alexander_Litvinenko Andrey Lugovo
  • 7. Do free TLS certificate make the internet more secure? https://letsencrypt.org/ http://www.infoworld.com/article/2984243/security/the-perils-of-free-digital-certificates.html#tk.ifw-infsb
  • 8. At the end of this presentation Know where to find data that supports how often certificate trust is broken Less blind trust in code signing Hold people and sites accountable for out of date / self signed certificates Align with the urgency to manage certificates in your environment Know about some tools
  • 9. • TLS 1.3 RFC expected in April 2016 • SHA1 no longer supported January 1, 2016 • NIST December 2015 • Google December 2015 • Microsoft June 2016 • Mozilla July 2016 Keynote: Alex Stamos The Moral Imperatives and Challenges for Modern Application Security https://www.youtube.com/watch?v=_xVoBA1f4gY Coming TLS changes
  • 10. Common TLS Certificates Trust Anchors • Website • Code Signing Certificates • S/MIME email encryption • Digital ID / User Identity • SSH • RDP • Business to Business Applications • VOIP • VPN • IoT
  • 11. Recent Code Signing Key Compromise News
  • 12. 10.28.15 Google to Symantec – “You have until June to fix this or we will flag Symantec issued certificates as vulnerable” We issued 23 test certificates That seems low, we don’t believe you Ok, your right it’s 2,458 Certificates http://arstechnica.com/security/2015/10/still-fuming-over-https-mishap-google-gives-symantec-an-offer-it-cant-refuse/
  • 14. • Komodia TLS intercept libraries • MITM HTTPS traffic • EFF Recommends reinstalling a fresh OS https://www.eff.org/deeplinks/2015/02/dear-software-vendors-please-stop-trying-intercept-your-customers-encrypted Considering that Lenovo implemented this intentionally and the potential damage, was this a criminal act ?
  • 15. Netcraft research indicates Certificate Authorities aren’t flagging domains with names that are similar to common, high traffic sites. Universal SSL certificates (free CloudFlare certificate) accounted for 40 percent of certificates used by phishing sites. http://www.infoworld.com/article/2992605/security/phishing-sites-exploit-trust-in-valid-ssl-certificates.html
  • 16. CRL (Certificate Revocation List ) • blacklist of revoked certificates • Often hard coded in the url • Often disabled because of the length of time to check OCSP (Online Certificate Status Protocol) • Improvement over CRL lists but the soft fail defeats the purpose OCSP Stapling best option • Requires implementation by Web Server Administrator to implement • SSLLabs.com OCSP Stapling will become a factor in your grade TLS Certificate Revocation
  • 17. And the bad guys know it doesn’t really work.... 8 % of the certificates being served had been revoked
  • 18. SANS Internet Storm Center https://isc.sans.edu/crls.html?token=e01d79423885ad9aac53ab92eb75274c116b548e&startdate=2014-10-04&enddate=2015-11-03&submit=Update
  • 20. OCSP Certificate Pinning OCSP Stapling requires the website administrators to enable it on their web server Certificate Transparency Add a layer of visibility to domain owners for CA issued TLS certificates. an open auditing and monitoring system that lets any domain owner or CA determine whether certificates have been mistakenly or maliciously issued. TACK Dynamic certificate framework. TACK requires protocol changes for both the server and the client side of any SSL transaction which has been met with a cold reception. Convergence Instead of hard coded CA’s. Convergence configures a dynamic set of Notaries. No incentive for the notary investment Sovereign Keys Addressed issues like the ineffectiveness of browser certificate warnings. Ended up just really replacing one remote authority with another. DANE DNS Authentication of Named Entities a proposal based on DNSSEC to eventually replace the CA system. It is based on the idea of using the DNS hierarchy to issue SSL certs the same way that domains are managed and resolved - with few root keys & individual organizations in charge. The challenge is that countries that have little trust would be required to trust the reliability of the DANE entry.
  • 22. OWASP OWASP Cheat Sheets OWASP Testing tools OWASP.org TLSSLed TLSSLed is Linux shell script to evaluate the security of target Kali Linux O-Saft OWASP SSL advanced forensic tool / OWASP SSL audit for testers https://www.owasp.org/index.php/O-Saft ssldump – An SSL/TLS network protocol analyzer It identifies TCP connections on the chosen network interface and attempts to interpret them as SSL/TLS traffic. When it identifies SSL/TLS traffic, it decodes the records and displays them in a textual form to stdout. If provided with the appropriate keying material, it will also decrypt the connections and display the application data traffic. http://ssldump.sourceforge.net/ SSLyze check for web SSL/TLS and also STARTTLS for smtp, xmpp, pop3, ftp, imap, ldap and rdp https://github.com/nabla-c0d3/sslyze SSL Server Test Provides a grade of a sites TLS implementation https://www.ssllabs.com/ssltest/ SSL Client Test Client TLS information https://www.ssllabs.com/ssltest/viewMy Client.html
  • 23. Prevention Ideal, Detection a Must ! But you won’t see this in your logs…… Censys Shodan Alexa Netcraft Google Hacks Internet Archives
  • 26. https://sonar.labs.rapid7.com/ Project Sonar Sonar collects SSL Certificates, Web Server responses, DNS records, and responses from common UDP services. We use this data to identify large-scale misconfigurations and vulnerabilities in consumer, enterprise, and critical infrastructure systems. All Sonar data is provided to the public free of charge in cooperation with the University of Michigan. You can find the data at Scans.IO.
  • 27. SSL/TLS Filters Cert Version Cert Bits Cert Issuer Cert Subject / Cert Name Check for known issues (Heartbleed) Cipher Bits / Protocol Grab cert for all services 27 Searches and indexes by responses to queries https://shodanio.wordpress.com/2014/06/16/kicking-the-shodan-api-up-a-notch/
  • 30. • What certificates are present on a given IP? • Which client IPs access a given service? Flying Pig – TLS Knowledge Base https://www.circl.lu/services/passive-ssl/
  • 31. http://blog.squarelemon.com/ DerbyCon TLS Fingerprinting Lee Brotherston @synackpse • Recognizing a TLS Fingerprint is possible by Capturing client TLS initial hello packets • Recognize SuperFish, PrivDog, and GeniusBox clients in network traffic “Using TLS fingerprinting we can quickly and passively determine which client is being used, and apply strategies from both the attacker and defender perspectives. These strategies allow us to achieve smarter defending and stealthier attacking” Lee Brotherston
  • 32. http://www.infoworld.com/article/2992605/security/phishing-sites-exploit-trust-in-valid-ssl-certificates.html Netcraft TLS Certificate Services Deceptive Domain Score analyzes the likelihood that a domain name will be used for fraudulent activities. Phishing Alert Service sends an alert if your site / certificate is used for a phishing scam
  • 33. Urgent need to proactively manage TLS Certificate inside and outside your firewall Think about code signing trust Hold people and sites accountable for out of date / self signed certificates Start now it’s going to get worse Summary
  • 34. OWASP https://owasp.org Cheat Sheets Key Pinning, TLS testing, CA Security Council https://casecurity.org/ is a multi-vendor industry advocacy group created to conduct research, promote Internet security standards and educate the public on Internet security issues. CA Browser (CAB) forum, which is a group that includes both CAs and web browser vendors. https://cabforum.org/ Voluntary consortium of certification authorities, vendors of Internet browser software, operating systems, and other PKI-enabled applications industry guidelines governing the issuance and management of X.509 v.3 digital certificates. Online Trust Alliance https://otalliance.org/resources/SSL/CABestPractice s.html European Telecommunications Standards Institute (ETSI) www.etsi.org independent, not-for-profit, standardization organization in the telecommunications industry) in Europe W3C http://www.w3.org/2001/tag/doc/web-https TAG’s position on securing the Web through the use of cryptography, identifies some of the associated issues, and recommends further work to aid in its use. Its primary audience is W3C participants
  • 35. Title Link PKI Trust Models: Whom Do You Trust https://www.sans.org/reading-room/whitepapers/vpns/pki-trust-models- trust-36112 Digital Certificate Revocation https://www.sans.org/reading-room/whitepapers/certificates/digital- certificate-revocation-35292 Building and Managing a PKI Solution for Small and Medium Size Business https://www.sans.org/reading-room/whitepapers/certificates/building- managing-pki-solution-small-medium-size-business-34445 SSl/TLS: What’s Under the Hood https://www.sans.org/reading-room/whitepapers/authentication/ssl-tls- hood-34297 Windows Enforcement of Authenticode Code Signing and Timestamping http://social.technet.microsoft.com/wiki/contents/articles/32288.windo ws-enforcement-of-authenticode-code-signing-and-timestamping.aspx The Scary and Terrible Code Signing Problem You Don’t Know You Have https://www.sans.org/reading-room/whitepapers/certificates/scary- terrible-code-signing-problem-don-039-t-36382 The Business Case For TLS Certificate Enterprise Key Management https://www.sans.org/reading-room/whitepapers/critical/business- case-tls-certificate-enterprise-key-management-web-site-certificates- wrangling-36392
  • 38. http://www.cs.utexas.edu/~shmat/shmat_ccs12.pdf We’ve focused on browser based TLS, there are many other applications that rely on TLS libraries and have validation challenges. More Work To do
  • 40. Sniffly Sniffly is an attack that abuses HTTP Strict Transport Security and Content Security Policy to allow arbitrary websites to sniff a user's browsing history. It has been tested in Firefox and Chrome https://github.com/diracdeltas/sniffly
  • 41. Highly classified decryption program run by the NSA The British signals intelligence agency GCHQ has a similar program codenamed Edgehill. http://www.spiegel.de/media/media-35531.pdf Bullrun

Editor's Notes

  • #3: Information Security Officer is similar to being a hostage negotiator Between the security team & the business (1) There is a lot of tension (2) You inform everyone of the law (3) Your fully aware that if people don't listen someone could die (4) you negotiate the ransom
  • #7: Died from poisoned tea
  • #8: Understand that providing free certificates is trying to solve one problem - but there is a cost – it creates other problems.
  • #9: Not just the code signing for your desktop and mobile applications but the code signatures that your business relies on as trust anchors
  • #10: Hashes are useful as long as they are unique. If two different message inputs generate the same hash (collision), then it is no longer safe information Counter perspective - Alex Stamos points out in his Moral Imperatives and Challenges for Modern Application Security Presentation that not supporting SHA1 will have a devastating effect on 3rd world countries that only have access to older technologies, for a threat that is “theoretical”
  • #12: It doesn’t break that often does it ? Umm it breaks a lot.
  • #13: CA need more transparency and accountability
  • #14: (1) This single expiring certificate caused collateral damage across multiple apps. What was broken was not easily discernible. Apple has yet to acknowledge what happened.
  • #18: GovRat is malware bundled with digital certificates for code signing and sold on TheRealDeal market place Hardcoding a URL very difficult for a long living certificates By the time DOD abandoned CRL checking in 2006 the CRL list was 200 MB (unlike CRLs and OCSP, which only involve the CA),
  • #21: CT helps with the detection problem by establishing a set of append-only public logs of certificates that anyone can audit. Individuals can submit observed certificates to public logs. Logs can be independently monitored to alert site owners when a new certificate for their site is entered in the log. This alerting will help a site owner quickly detect certain types of miss-issuance and get any miss-issued certificates revoked. In Chrome, CT is required for all new EV certificates.
  • #29: Even though Censys much better for certificate search / Shodan provides other certificate finds
  • #30: More search tool options
  • #31: The NSA Flying Pig program inspiration for the CIRCL Passive SSL project
  • #33: These service from Netcraft are another defensive tool that could be enormously beneficial depending on environmental risk.
  • #34: Not just the code signing for your desktop and mobile applications but the code signatures that your business relies on as trust anchors
  • #41: Another consideration is the leaked TLS client data. Another way to track people.
  • #42: Snowden documentation provided insight into how active government