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PUTTING RUGGED INTO
YOUR DEVOPS TOOLCHAIN
  JAMES WICKETT, @WICKETT
I WANT YOU TO BE
SUCCESSFUL AND
MAKE A DIFFERENCE
James Wickett
CISSP, GWAPT,
CCSK, GSEC, GCFW
  @wickett
@RuggedDevOps
  @gauntlt
HTTP://BIT.LY/RUGGED-DEVOPS
A BRIEF HISTORY OF
INFORMATION SECURITY
WE USED TO BE COOL
WE HAD
CINEMA
WE HAD
HEROES
WE MADE FREE
PHONE CALLS
WE WERE COOL
WE MADE IT INTO THE
ORGANIZATIONS
WE HAD PREVIOUSLY FOUGHT
WE HELD CONFERENCES
IN FANCY HOTELS
WHERE WE CLAIMED WE HAD
NO BUSINESS SUPPORT
WE HAVE BUSINESS CARDS
WITH TITLES LIKE
CISO ON THEM
ONCE IN THE ORG
INFOSEC MADE
BIG CLAIMS
WE COULDN’T STOP THE
VIRUSES AND WORMS
ENTER RISK
ASSESSMENT
INSTEAD OF ENGINEERING
INFOSEC BECAME ACTUARIES
WE BECAME EXPERTS
IN BUYING INSURANCE POLICIES
“[RISK ASSESSMENT] INTRODUCES A
DANGEROUS FALLACY: THAT
STRUCTURED INADEQUACY IS
ALMOST AS GOOD AS ADEQUACY
AND THAT UNDERFUNDED
SECURITY EFFORTS PLUS RISK
MANAGEMENT ARE ABOUT AS
GOOD AS PROPERLY FUNDED
SECURITY WORK” - MICHAL ZALEWSKI
WE MADE A
SIGNIFICANT
ERROR
WE THOUGHT THIS WAS TRUE:
EVERY SECURITY EVENT
RESULTS IN A FINANCIAL LOSS
TJX H@CK3D!
THE STOCK PRICE
DIDN’T DROP
OUR ASSUMPTION
WAS INCOMPLETE
INFOSEC ALSO MADE
A SECOND BIG MISTAKE
IT STAYED IN
INFORMATION
TECHNOLOGY
IT WAS A COST CENTER
AND NOT IN A POSITION
TO ADD VALUE
SOMETHING ELSE
HAPPENED GLOBALLY
DEVS BECAME COOL
CODE BECAME SOCIAL
“I DON’T WANT YOU
TO SEND ME AN
INSTALLATION DVD”
WE SELL TIME NOW
WE SELL SOCIAL
AND FRIENDSHIPS
“IS THIS SECURE?”
-YOUR CUSTOMER
“ITS CERTIFIED”- YOU
WHY CAN’T YOU
GIVE A BETTER ANSWER?
THE INEQUITABLE
DISTRIBUTION OF
LABOR IN SECURITY
MIMICS THAT IN DEV/OPS
source: Gene Kim, “When IT says No @SXSW 2012”
Security sees...
• They give advice that goes unheeded
• Business decisions made w/o regard of risk
• Irrelevancy in the organization
• Constant bearer of bad news
• Feels ignored by their peers (you know,
  those devops guys)
• Inequitable distribution of labor
2% OF AN ENGINEERING
DEV TEAM ARE WORKING
ON SECURITY
    - BSIMM 2012 data, http://bsimm.com/
HOW DO WE FIX
THESE PROBLEMS?
-LEARNING FROM
(PREFERABLY OTHER
PEOPLE’S) MISTAKES
-DEVELOPING TOOLS TO
CORRECT PROBLEMS
- PLANNING TO HAVE
EVERYTHING
COMPROMISED
UNDERSTANDING
TOOLING
ARCHITECTURE
OPEN WEB APPLICATION
SECURITY PROJECT
Current Software
Rugged Software
Current Software
Rugged Software
Current Software
Rugged Software
ADVERSITY REQUIRES
RUGGED SOLUTIONS
ADVERSITY IS REAL OR
PERCEIVED NEGATIVE
ACTIONS AND EVENTS
THAT PROHIBIT NORMAL
FUNCTION AND OPERATION.
Building solutions to handle
    adversity will cause
    unintended, positive benefits
    that will provide value that
    would have been unrealized
    otherwise.
    RUGGEDIZATION
       THEORY
NO PAIN, NO GAIN
"Secondly, our network
 got a lot stronger as a
  result of the LulzSec
        attacks."
-Surviving Lulz: Behind the Scenes of LulzSec @SXSW 2012
                     by CloudFlare team
REPEATABLE – NO MANUAL STEPS
RELIABLE - NO DOS HERE
REVIEWABLE – AKA AUDIT
RAPID – FAST TO BUILD, DEPLOY, RESTORE
RESILIENT – AUTOMATED RECONFIGURATION
REDUCED - LIMITED ATTACK SURFACE
RUGGED BY DESIGN,
DEVOPS BY CULTURE
RUGGED DEVOPS
Put your code through
      the gauntlt
GAUNTLET, N.
AN ATTACK FROM
ALL SIDES
custom attacks   dirbuster
   metasploit             sqlmap

  fuzzers                      nessus

w3af                                nmap




 Your web app            You
gauntlt is built for doing security
   testing in a DevOps world
GAUNTLT IS
AN ALWAYS-
ATTACKING
ENVIRONMENT FOR
DEVELOPERS
WITH ATTACKS
WRITTEN IN
EASY-TO-READ
LANGUAGE
ACCESSIBLE TO
EVERYONE INVOLVED
IN DEV, OPS,
TESTING, SECURITY, ...
MEET THE GAUNTLT
TEAM
MANI
TADAYON
"SOFTWARE -
WAR = SOFTE"
@BWSR_SR
ROY
RAPOPORT
“I PICKED UP THE TEE
SHIRTS”

@ROYRAPOPORT
BILL BURNS
@X509V3
“SMITHERS,
RELEASE THE
MONKEYS!”
JOSHUA
CORMAN
@JOSHCORMAN
@RUGGEDSOFTWARE

“HONEY BADGER
DOES CARE” 
JASON
CHAN
@CHANJBS
NOT PICTURED:
MATT TESAURO
TAREK MOUSSA
WHY GAUNTLT?

SECURITY DOMAIN
KNOWLEDGE IS GENERALLY
A MYSTERY TO DEV TEAMS
GAUNTLT ALLOWS DEV AND
OPS AND SECURITY TO
COMMUNICATE
GAUNTLT JOINS
THE PHILOSOPHY OF
RUGGED SOFTWARE
& CONTINUOUS INTEGRATION
HTTPS://GITHUB.COM/THEGAUNTLET/GAUNTLT
LETS LOOK INSIDE A
COUPLE OF THESE FILES
feature for nmap:
                     nmap.feature
@gauntlet @run

Feature: Run nmap against a target and pass the value of the hostname from the profile.xml.

Background:
 Given nmap is installed

Scenario:Verify server is available on standard web ports
 Given the hostname in the profile.xml
 When I run nmap against the hostname in the profile on ports 80,443
 Then the output should contain:
  """
  80/tcp open http
  443/tcp open https
  """
step definition for nmap:
                 nmap.rb
Given /^nmap is installed$/ do
 steps %{
   When I run `which nmap`
   Then the output should contain:
   """
   nmap
   """
 }
end

When /^I run nmap against the hostname in the profile on ports (d+),(d+)$/ do |arg2, arg3|
 steps %{
   When I run `nmap "#{@hostname}" -p80,443`
 }
end
running gauntlt with failing tests
wickett$ gauntlt

@gauntlet @run
Feature: Run nmap against a target and pass the value of the hostname from the profile.xml.

 Background:           # features/nmap/nmap.feature:5
  Given nmap is installed # features/step_definitions/nmap.rb:2

   Scenario:Verify server is available on standard web ports       # features/nmap/nmap.feature:8
    Given the hostname in the profile.xml                       # features/step_definitions/profile.rb:1
    When I run nmap against the hostname in the profile on ports 8080,443 # features/step_definitions/nmap.rb:12
    Then the output should contain:                          # aruba-0.4.11/lib/aruba/cucumber.rb:98
     """
     8080/tcp open http
     443/tcp open https
     """
...

Failing Scenarios:
cucumber features/nmap/nmap.feature:8 # Scenario:Verify server is available on standard web ports

1 scenario (1 failed)
4 steps (1 failed, 3 passed)
0m0.341s
running gauntlt with passing tests
wickett$ gauntlt

@gauntlet @run
Feature: Run nmap against a target and pass the value of the hostname from the profile.xml.

 Background:           # features/nmap/nmap.feature:5
  Given nmap is installed # features/step_definitions/nmap.rb:2

 Scenario:Verify server is available on standard web ports       # features/nmap/nmap.feature:8
  Given the hostname in the profile.xml                       # features/step_definitions/profile.rb:1
  When I run nmap against the hostname in the profile on ports 80,443 # features/step_definitions/nmap.rb:12
  Then the output should contain:                          # aruba-0.4.11/lib/aruba/cucumber.rb:98
   """
   80/tcp open http
   443/tcp open https
   """

1 scenario (1 passed)
4 steps (4 passed)
0m1.117s
RESOURCES
WANT TO JOIN THE
GAUNTLT TEAM?
EMAIL JAMES@RUGGEDDEVOPS.ORG
Please get in
touch with me:
@wickett
@RuggedDevOps
@gauntlt

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Putting Rugged Into your DevOps Toolchain