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Robots, Ninjas, Pirates and
Building an Effective Vulnerability
Management Program
© Copyright Defensive Intuition, LLC 2004-2015
Paul Asadoorian
Day: Product Strategist, Tenable Network Security
Nights & Weekends: Founder & CEO, Security Weekly
© Copyright Defensive Intuition, LLC 2004-2015 Slide 2
About Paul
Agenda
• Some slides with random pictures from the Internet
• Paul talks about vulnerability management over said slides
• Folks may have questions or challenge my thoughts/ideas
(please do)
• More random Internet pictures
• Paul ranting a bit more while laughing at ridiculous pictures
• These are the only bullets in this presentation…
• End with tips on how to be successful
© Copyright Defensive Intuition, LLC 2004-2015 Slide 3
Vulnerability Management…
© Copyright Defensive Intuition, LLC 2004-2015 Slide 4
You have all the right tools…
A Robot, Ninja & Pirate Get
Into a Fight, Who Wins?
© Copyright Defensive Intuition, LLC 2004-2015 Slide 5
We have arguments like this all the
time.	

!
Sometimes they center around
vulnerability management…
Why Do We Need Vulnerability
Management?
© Copyright Defensive Intuition, LLC 2004-2015 Slide 6
You
The Internet
Don’t Be Blind…
You can’t fix what you don’t know is broken…
© Copyright Defensive Intuition, LLC 2004-2015
Meet The Robots, Ninjas and
Pirates in the Security Dept.
© Copyright Defensive Intuition, LLC 2004-2015
The Robot
Without a care in the world…
© Copyright Defensive Intuition, LLC 2004-2015
“Going to scan the
network!”
The Robot
Cares even less how long the report will be…
© Copyright Defensive Intuition, LLC 2004-2015
File -> Print…
Reporting!!!!
The Robot
What your network looks like after the scan…
© Copyright Defensive Intuition, LLC 2004-2015
The Robot
What the sysadmins, network admins, developers, help desk and
operations are saying about you…
© Copyright Defensive Intuition, LLC 2004-2015
Robots reporting to management
© Copyright Defensive Intuition, LLC 2004-2015
“The chances of cross-site scripting being
exploited are 725 to 1. Its quite possible the buffer
overflow attacks aren’t quite stable.The odds of
successfully surviving an attack on the Apache web server
are…[Shut up 3po!].They’ve encased the web server in a
WAF, it should be quite well protected, unless there is a
bypass. I noticed the IPS pre-processor rules are
damaged, its impossible to block attacks.”
Moral of the story…
© Copyright Defensive Intuition, LLC 2004-2015
The Ninjas
© Copyright Defensive Intuition, LLC 2004-2015
Wrote
Nmap script
to patch
everything and
disable
TELNET.
The Report
© Copyright Defensive Intuition, LLC 2004-2015
The Network
Problems can be mysterious….
© Copyright Defensive Intuition, LLC 2004-2015
Sysadmins be like…
Sysadmins be like…
© Copyright Defensive Intuition, LLC 2004-2015
Ninjas be like…
© Copyright Defensive Intuition, LLC 2004-2015
Pirates
To find the booty…
© Copyright Defensive Intuition, LLC 2004-2015
I’m gonna scan
your network.
Hard.
During the scan…
© Copyright Defensive Intuition, LLC 2004-2015
The Report
© Copyright Defensive Intuition, LLC 2004-2015
+
Pirate in meeting after report has been distributed
© Copyright Defensive Intuition, LLC 2004-2015
Patch your shit!
Aaaaaaaaaarrgh!!
Pirates Lack Social Skillz
Sysadmins: Fear them…
© Copyright Defensive Intuition, LLC 2004-2015
Meet the Robots, Ninja and
Pirate Attackers
© Copyright Defensive Intuition, LLC 2004-2015
Perception Of Scanning
Even a broken clock is right twice a day
© Copyright Defensive Intuition, LLC 2004-2015
“Your slave?”
“You wish!You'll do
shitwork, scan, crack
copyrights…"
Attackers, like robots,
automate…
Attacks above are common, but less severe (typically)
© Copyright Defensive Intuition, LLC 2004-2015
Or APT, or Cyber<something>
© Copyright Defensive Intuition, LLC 2004-2015
Ninjas
© Copyright Defensive Intuition, LLC 2004-2015
Cyber Pirate Attackers
Pirates will steal bandwidth, often very loud.
© Copyright Defensive Intuition, LLC 2004-2015
Now We Understand Some Of
The Dynamics
What we learned up to this point:
!
Vulnerability Management is HARD, attackers will not let up.
© Copyright Defensive Intuition, LLC 2004-2015
© Copyright Defensive Intuition, LLC 2004-2015 Slide 32
Shortcuts Are Trouble
“We’ll just scan once per quarter”
!
“We can just use the default scan policy”
!
“We can just scan parts of the network”
© Copyright Defensive Intuition, LLC 2004-2015
© Copyright Defensive Intuition, LLC 2004-2015
“We don’t care about finding all the
vulnerabilities. Just show me the important
ones. I can’t fix everything, so don’t bother
showing me everything.”
5 Reasons Why This Will End
Badly
© Copyright Defensive Intuition, LLC 2004-2015
#1 What you don’t know will
probably be the thing that
hurts you
© Copyright Defensive Intuition, LLC 2004-2015
#2 Ask any evil bad guy or
penetration tester and they
will tell you “we string
together seemingly low
severity vulnerabilities to
achieve a goal”
© Copyright Defensive Intuition, LLC 2004-2015
Example: Chris Gates from Low to Pwned (2012) https://
www.youtube.com/watch?v=u68QvWXYW_Q
#3 External conditions
change, so not patching a
vulnerabilities because there
is no public exploit today
doesn’t mean there will not
be an exploit in the future (or
someone has it already)
© Copyright Defensive Intuition, LLC 2004-2015
#4 Internal conditions
change. Not discovering
vulnerabilities in XYZ
software because you don’t
use XYZ software is
dangerous
!
Someone could be installing
XYZ software as we speak
© Copyright Defensive Intuition, LLC 2004-2015
For Example…
© Copyright Defensive Intuition, LLC 2004-2015
#5 Vulnerability
management is a historical
reference.
!
You may not care which USB
device were plugged into
your systems today, but
when malware spreads via
USB devices tomorrow…
© Copyright Defensive Intuition, LLC 2004-2015
Malware Here?
© Copyright Defensive Intuition, LLC 2004-2015
!
“Just send them
the raw results”
!
“Just patch CVSS
> 8.0”
Goals & Results Matter…
© Copyright Defensive Intuition, LLC 2004-2015
Results Matter, Don’t Be Lazy
No one reads raw results
© Copyright Defensive Intuition, LLC 2004-2015
Can You Make That 8 a 7?
CVSS is subjective
© Copyright Defensive Intuition, LLC 2004-2015
Vulnerability
Management
Goals
© Copyright Defensive Intuition, LLC 2004-2015
Goal: Prevention – prevent
bad things with the resources
you have
© Copyright Defensive Intuition, LLC 2004-2015
Stop waiting around
for the perfect
solution!
Goal:
Detection
!
Know
where you
are
vulnerable
and monitor
© Copyright Defensive Intuition, LLC 2004-2015
Goal: React - Define priorities
and enable people to take
action
Vulnerability management is a repeatable process.
© Copyright Defensive Intuition, LLC 2004-2015
Goal: Do it
yourself.
!
Vulnerability
scanning is not
what a pen
tester should
do for you
Tools have matured to allow for continuous scanning.
© Copyright Defensive Intuition, LLC 2004-2015
Goal: Evaluate tools – Define
the evaluation criteria
Virtualization, Cloud, Mobile, Patch Management, Agents, Web Apps.
© Copyright Defensive Intuition, LLC 2004-2015
Goal: Checks and Balances:
How are my other defenses
working or not?
Anti-Virus, Firewalls, Compliance/System Hardening Programs
© Copyright Defensive Intuition, LLC 2004-2015
Goal: Metrics: Don’t Give Up
On Them
© Copyright Defensive Intuition, LLC 2004-2015
Searches for “dating tips”
Searches for “fleshlight”
What does
management
want to see?
Goal: Threat Modeling
© Copyright Defensive Intuition, LLC 2004-2015
Goal: Don’t just find a
standard or copy what may
work for others
Be a LEADER and set your own standards.
© Copyright Defensive Intuition, LLC 2004-2015
Goal: Get people to
understand and change their
behavior
Become a remarkable IT Security Leader
© Copyright Defensive Intuition, LLC 2004-2015
Some Fun Facts
Podcasts/Blogs/Videos: http://securityweekly.com
Contact Me: paul@securityweekly.com
© Copyright Defensive Intuition, LLC 2004-2015
http://securityweekly.com/attend
Security Weekly & Tenable are always hiring.
!
You can some to our studio on Thursday nights and watch the show
live.
!
I post all my slides to http://slideshare.net/securityweekly
!
Larry really does have a tattoo in “that place”.
!
Jack is really old.
!
Also, Ninja is the winner.

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Robots, Ninjas, Pirates and Building an Effective Vulnerability Management Program

  • 1. Robots, Ninjas, Pirates and Building an Effective Vulnerability Management Program © Copyright Defensive Intuition, LLC 2004-2015 Paul Asadoorian Day: Product Strategist, Tenable Network Security Nights & Weekends: Founder & CEO, Security Weekly
  • 2. © Copyright Defensive Intuition, LLC 2004-2015 Slide 2 About Paul
  • 3. Agenda • Some slides with random pictures from the Internet • Paul talks about vulnerability management over said slides • Folks may have questions or challenge my thoughts/ideas (please do) • More random Internet pictures • Paul ranting a bit more while laughing at ridiculous pictures • These are the only bullets in this presentation… • End with tips on how to be successful © Copyright Defensive Intuition, LLC 2004-2015 Slide 3
  • 4. Vulnerability Management… © Copyright Defensive Intuition, LLC 2004-2015 Slide 4 You have all the right tools…
  • 5. A Robot, Ninja & Pirate Get Into a Fight, Who Wins? © Copyright Defensive Intuition, LLC 2004-2015 Slide 5 We have arguments like this all the time. ! Sometimes they center around vulnerability management…
  • 6. Why Do We Need Vulnerability Management? © Copyright Defensive Intuition, LLC 2004-2015 Slide 6 You The Internet
  • 7. Don’t Be Blind… You can’t fix what you don’t know is broken… © Copyright Defensive Intuition, LLC 2004-2015
  • 8. Meet The Robots, Ninjas and Pirates in the Security Dept. © Copyright Defensive Intuition, LLC 2004-2015
  • 9. The Robot Without a care in the world… © Copyright Defensive Intuition, LLC 2004-2015 “Going to scan the network!”
  • 10. The Robot Cares even less how long the report will be… © Copyright Defensive Intuition, LLC 2004-2015 File -> Print… Reporting!!!!
  • 11. The Robot What your network looks like after the scan… © Copyright Defensive Intuition, LLC 2004-2015
  • 12. The Robot What the sysadmins, network admins, developers, help desk and operations are saying about you… © Copyright Defensive Intuition, LLC 2004-2015
  • 13. Robots reporting to management © Copyright Defensive Intuition, LLC 2004-2015 “The chances of cross-site scripting being exploited are 725 to 1. Its quite possible the buffer overflow attacks aren’t quite stable.The odds of successfully surviving an attack on the Apache web server are…[Shut up 3po!].They’ve encased the web server in a WAF, it should be quite well protected, unless there is a bypass. I noticed the IPS pre-processor rules are damaged, its impossible to block attacks.”
  • 14. Moral of the story… © Copyright Defensive Intuition, LLC 2004-2015
  • 15. The Ninjas © Copyright Defensive Intuition, LLC 2004-2015 Wrote Nmap script to patch everything and disable TELNET.
  • 16. The Report © Copyright Defensive Intuition, LLC 2004-2015
  • 17. The Network Problems can be mysterious…. © Copyright Defensive Intuition, LLC 2004-2015
  • 18. Sysadmins be like… Sysadmins be like… © Copyright Defensive Intuition, LLC 2004-2015
  • 19. Ninjas be like… © Copyright Defensive Intuition, LLC 2004-2015
  • 20. Pirates To find the booty… © Copyright Defensive Intuition, LLC 2004-2015 I’m gonna scan your network. Hard.
  • 21. During the scan… © Copyright Defensive Intuition, LLC 2004-2015
  • 22. The Report © Copyright Defensive Intuition, LLC 2004-2015 +
  • 23. Pirate in meeting after report has been distributed © Copyright Defensive Intuition, LLC 2004-2015 Patch your shit! Aaaaaaaaaarrgh!! Pirates Lack Social Skillz
  • 24. Sysadmins: Fear them… © Copyright Defensive Intuition, LLC 2004-2015
  • 25. Meet the Robots, Ninja and Pirate Attackers © Copyright Defensive Intuition, LLC 2004-2015
  • 26. Perception Of Scanning Even a broken clock is right twice a day © Copyright Defensive Intuition, LLC 2004-2015 “Your slave?” “You wish!You'll do shitwork, scan, crack copyrights…"
  • 27. Attackers, like robots, automate… Attacks above are common, but less severe (typically) © Copyright Defensive Intuition, LLC 2004-2015
  • 28. Or APT, or Cyber<something> © Copyright Defensive Intuition, LLC 2004-2015
  • 29. Ninjas © Copyright Defensive Intuition, LLC 2004-2015
  • 30. Cyber Pirate Attackers Pirates will steal bandwidth, often very loud. © Copyright Defensive Intuition, LLC 2004-2015
  • 31. Now We Understand Some Of The Dynamics What we learned up to this point: ! Vulnerability Management is HARD, attackers will not let up. © Copyright Defensive Intuition, LLC 2004-2015
  • 32. © Copyright Defensive Intuition, LLC 2004-2015 Slide 32 Shortcuts Are Trouble
  • 33. “We’ll just scan once per quarter” ! “We can just use the default scan policy” ! “We can just scan parts of the network” © Copyright Defensive Intuition, LLC 2004-2015
  • 34. © Copyright Defensive Intuition, LLC 2004-2015 “We don’t care about finding all the vulnerabilities. Just show me the important ones. I can’t fix everything, so don’t bother showing me everything.”
  • 35. 5 Reasons Why This Will End Badly © Copyright Defensive Intuition, LLC 2004-2015
  • 36. #1 What you don’t know will probably be the thing that hurts you © Copyright Defensive Intuition, LLC 2004-2015
  • 37. #2 Ask any evil bad guy or penetration tester and they will tell you “we string together seemingly low severity vulnerabilities to achieve a goal” © Copyright Defensive Intuition, LLC 2004-2015 Example: Chris Gates from Low to Pwned (2012) https:// www.youtube.com/watch?v=u68QvWXYW_Q
  • 38. #3 External conditions change, so not patching a vulnerabilities because there is no public exploit today doesn’t mean there will not be an exploit in the future (or someone has it already) © Copyright Defensive Intuition, LLC 2004-2015
  • 39. #4 Internal conditions change. Not discovering vulnerabilities in XYZ software because you don’t use XYZ software is dangerous ! Someone could be installing XYZ software as we speak © Copyright Defensive Intuition, LLC 2004-2015
  • 40. For Example… © Copyright Defensive Intuition, LLC 2004-2015
  • 41. #5 Vulnerability management is a historical reference. ! You may not care which USB device were plugged into your systems today, but when malware spreads via USB devices tomorrow… © Copyright Defensive Intuition, LLC 2004-2015
  • 42. Malware Here? © Copyright Defensive Intuition, LLC 2004-2015
  • 43. ! “Just send them the raw results” ! “Just patch CVSS > 8.0” Goals & Results Matter… © Copyright Defensive Intuition, LLC 2004-2015
  • 44. Results Matter, Don’t Be Lazy No one reads raw results © Copyright Defensive Intuition, LLC 2004-2015
  • 45. Can You Make That 8 a 7? CVSS is subjective © Copyright Defensive Intuition, LLC 2004-2015
  • 47. Goal: Prevention – prevent bad things with the resources you have © Copyright Defensive Intuition, LLC 2004-2015 Stop waiting around for the perfect solution!
  • 48. Goal: Detection ! Know where you are vulnerable and monitor © Copyright Defensive Intuition, LLC 2004-2015
  • 49. Goal: React - Define priorities and enable people to take action Vulnerability management is a repeatable process. © Copyright Defensive Intuition, LLC 2004-2015
  • 50. Goal: Do it yourself. ! Vulnerability scanning is not what a pen tester should do for you Tools have matured to allow for continuous scanning. © Copyright Defensive Intuition, LLC 2004-2015
  • 51. Goal: Evaluate tools – Define the evaluation criteria Virtualization, Cloud, Mobile, Patch Management, Agents, Web Apps. © Copyright Defensive Intuition, LLC 2004-2015
  • 52. Goal: Checks and Balances: How are my other defenses working or not? Anti-Virus, Firewalls, Compliance/System Hardening Programs © Copyright Defensive Intuition, LLC 2004-2015
  • 53. Goal: Metrics: Don’t Give Up On Them © Copyright Defensive Intuition, LLC 2004-2015 Searches for “dating tips” Searches for “fleshlight” What does management want to see?
  • 54. Goal: Threat Modeling © Copyright Defensive Intuition, LLC 2004-2015
  • 55. Goal: Don’t just find a standard or copy what may work for others Be a LEADER and set your own standards. © Copyright Defensive Intuition, LLC 2004-2015
  • 56. Goal: Get people to understand and change their behavior Become a remarkable IT Security Leader © Copyright Defensive Intuition, LLC 2004-2015
  • 57. Some Fun Facts Podcasts/Blogs/Videos: http://securityweekly.com Contact Me: paul@securityweekly.com © Copyright Defensive Intuition, LLC 2004-2015 http://securityweekly.com/attend Security Weekly & Tenable are always hiring. ! You can some to our studio on Thursday nights and watch the show live. ! I post all my slides to http://slideshare.net/securityweekly ! Larry really does have a tattoo in “that place”. ! Jack is really old. ! Also, Ninja is the winner.