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New Farming Methods
in the Epistemological
Wasteland of
Application Security
- @wickett
@wickett #ruggeddevops
bit.ly/rdo-farming
Slides
@wickett #ruggeddevops
James Wickett
SR. ENGINEER, SIGNAL SCIENCES
AUSTIN, TX
HANDS-ON GAUNTLT BOOK
DEVOPS DAYS GLOBAL ORGANIZER
LASCON ORGANIZER
Application Security Telemetry and Monitoring
Plus Defense!
Application Security for the rest of us
An approach that integrates with devops
organizations doesn't inhibit going fast
5
@wickett #ruggeddevops
@wickett #ruggeddevops
Software development is a constant experiment in knowing
Application Security abdicated runtime responsibility and
development responsibility through incoherent
philosophical approaches and fostering silo-thinking
Security now is where Ops was 7 years ago.
Ops found a path to change through devops, security can
too
There are three ways we can add value: at development, at
deploy, at runtime
Summary
@wickett #ruggeddevops
Bad-Behavior Driven Development
Weaponizing your CD Pipeline
Application Security Telemetry and Monitoring
Continuous Hardening and Audit
Have a S-BOM! (Software Bill of Materials)
Practices
@wickett #ruggeddevops
Where do we
come from
@wickett #ruggeddevops
A study in how we
know anything in
Application Security
@wickett #ruggeddevops
Spoiler Alert:
We don’t !
@wickett #ruggeddevops
once upon a time…
@wickett #ruggeddevops
What does it all mean?
A Journey to the
Epistemological
Problem of Software
Development
@wickett #ruggeddevops
In our Innate Humanness
We optimize for the
probable
@wickett #ruggeddevops
Unit Testing
@wickett #ruggeddevops
Integration Testing
@wickett #ruggeddevops
Happy Path
Engineering
@wickett #ruggeddevops
We also optimize
for the possible
@wickett #ruggeddevops
Over Engineering
@wickett #ruggeddevops
The scaling algo
that never got used…
@wickett #ruggeddevops
There is too much to
choose from in the
realm of possible
@wickett #ruggeddevops
Actually, we optimize for
the perceived probable
@wickett #ruggeddevops
How do we know
what to create?
@wickett #ruggeddevops
This is the problem
@wickett #ruggeddevops
Epistemological
Problem of Software
Development
@wickett #ruggeddevops
We gather data and
rhetoric to support
our theories
@wickett #ruggeddevops
There are 3 major
arcs currently in
Software Development
@wickett #ruggeddevops
We started as Civil
Engineers
@wickett #ruggeddevops
First Arc:
Agile
@wickett #ruggeddevops
Agile avoids the
problem
@wickett #ruggeddevops
Agile reminds that
we dont know what
we are building
@wickett #ruggeddevops
@wickett #ruggeddevops
Behavior Driven
Development
@wickett #ruggeddevops
BDD = Agile +
feedback
@wickett #ruggeddevops
Behavior Driven Development is a
second-generation, outside–in, pull-
based, multiple-stakeholder, multiple-
scale, high-automation, agile
methodology. It describes a cycle of
interactions with well-defined
outputs, resulting in the delivery of
working, tested software that matters.
Dan North , 2009
@wickett #ruggeddevops
Amplify
Feedback
Loop
@wickett #ruggeddevops
Agile emphasizes
feedback to developers
from their overlords and
sometimes even customers
@wickett #ruggeddevops
TLDR;
Rapid Iterations Win
@wickett #ruggeddevops
Agile is
our guiding
Light
@wickett #ruggeddevops
The world has
changed since Agile
@wickett #ruggeddevops
We don’t sell
CD’s anymore
@wickett #ruggeddevops
Software as a
Service
@wickett #ruggeddevops
The last fifteen years have
brought a complete change in
our delivery cadence,
distribution mechanisms and
revenue models
@wickett #ruggeddevops
Second Arc: DevOps
@wickett #ruggeddevops
DEVOPS IS THE APPLICATION OF
AGILE METHODOLOGY TO SYSTEM
ADMINISTRATION
- THE PRACTICE OF CLOUD SYSTEM ADMINISTRATION BOOK
@wickett #ruggeddevops
DEVOPS
@wickett #ruggeddevops
Agile
Infrastructure
@wickett #ruggeddevops
http://www.slideshare.net/jallspaw/10-deploys-per-day-dev-and-ops-cooperation-at-flickr
@wickett #ruggeddevops
Less WIP
Less technical debt
@wickett #ruggeddevops
Customers actually using
the feature while the
developer is working on it
@wickett #ruggeddevops
Great side effect:
Produces Happy Developers
@wickett #ruggeddevops
@wickett #ruggeddevops
@wickett #ruggeddevops
Devops realized that ops
doesn’t know what devs
know and vice versa
@wickett #ruggeddevops
Dev : Ops
10 : 1
@wickett #ruggeddevops
DevOps is an Epistemological
breakthrough joining people
around a common problem
@wickett #ruggeddevops
Culture is the most
important aspect to devops
succeeding in the enterprise
- Patrick DeBois
@wickett #ruggeddevops
Culture is shaped in
part by values
@wickett #ruggeddevops
@wickett #ruggeddevops
Mutual Understanding
Shared Language
Shared Views
Collaborative Tooling
@wickett #ruggeddevops
DEVOPS IS THE INEVITABLE RESULT OF NEEDING
TO DO EFFICIENT OPERATIONS IN A [DISTRIBUTED
COMPUTING AND CLOUD] ENVIRONMENT.
- TOM LIMONCELLI
@wickett #ruggeddevops
https://puppetlabs.com/sites/default/files/2015-state-of-devops-report.pdf
@wickett #ruggeddevops
TLDR;
High-performing IT
organizations experience 60X
fewer failures and recover from
failure 168X faster than their
lower-performing peers. They
also deploy 30X more frequently
with 200X shorter lead times.
@wickett #ruggeddevops
Culture
Automation
Measurement
Sharing
- @damonedwards, @botchagalupe
@wickett #ruggeddevops
Devops gone wrong
@wickett #ruggeddevops
“THAT THE WORD #DEVOPS GETS REDUCED
TO TECHNOLOGY IS A MANIFESTATION OF
HOW BADLY WE NEED A CULTURAL SHIFT”
- @PATRICKDEBOIS
http://www.slideshare.net/cm6051/london-devops-31-5-years-of-devops
@wickett #ruggeddevops
Third Arc:
Continuous
Delivery
@wickett #ruggeddevops
Continuous Delivery is not
merely how often you
deliver but how little
you can deliver at a time
@wickett #ruggeddevops
Delivery
Pipelines
are rad!
@wickett #ruggeddevops
Batch Size of 1
@wickett #ruggeddevops
Separation of Duties
Considered Harmful
@wickett #ruggeddevops
Give power to the
Developers to deploy
@wickett #ruggeddevops
Reduce Code Latency
Increase Code Velocity
@wickett #ruggeddevops
3 Arcs:
Agile
DevOps
Continuous Delivery
@wickett #ruggeddevops
The next Arc:
Security
Rugged
@wickett #ruggeddevops
“…Those stupid developers”
- Security person
@wickett #ruggeddevops
“Security prefers a system
powered off and unplugged”
- Developer
@wickett #ruggeddevops
Cultural Unrest
with security in
most organizations
@wickett #ruggeddevops
Compliance Driven
Culture
@wickett #ruggeddevops
“[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”
@wickett #ruggeddevops
Security is where ops
was 7 years ago…
@wickett #ruggeddevops
Dev : Ops : Sec
100 : 10 : 1
@wickett #ruggeddevops
Understaffing means
no one thinks security
helps the business win
@wickett #ruggeddevops
DevOps changed that
for Ops, security can
change too
@wickett #ruggeddevops
Netflix
demonstrated
that people
care about
resiliency
@wickett #ruggeddevops
Innately, we all care
@wickett #ruggeddevops
Rugged Software Movement
@wickett #ruggeddevops
#ruggeddevops
@wickett #ruggeddevops
https://vimeo.com/54250716
@wickett #ruggeddevops
http://www.youtube.com/watch?v=jQblKuMuS0Y
@wickett #ruggeddevops
Security’s way forward is to
help developers and help
operations
@wickett #ruggeddevops
Start there
@wickett #ruggeddevops
Let’s review Security’s
approach thus far
@wickett #ruggeddevops
BadIdea #1
Applications can’t be
defended—Web App
Firewalls Suck!
lets do developer training
@wickett #ruggeddevops
@wickett #ruggeddevops
@wickett #ruggeddevops
Awareness campaign
OWASP Top Ten
@wickett #ruggeddevops
We abandoned knowing
anything useful about
the Runtime
@wickett #ruggeddevops
Instead Add Defense
based on behaviors
@wickett #ruggeddevops
BadIdea #2
Developers can’t figure it out.
lets scan for vulnerabilities
instead
@wickett #ruggeddevops
“here is a 400 page PDF of
our findings to prove your
developers don't get it!”
- The Pen tester
@wickett #ruggeddevops
Even with the emphasis
on appsec training, in
practice we made it a
dark art
@wickett #ruggeddevops
Integrated rugged
testing should sit
inside the pipeline
@wickett #ruggeddevops
BadIdea #3
With the new alignment
to vulnerability scanning,
there is a tendency to Fix
the Low-Hanging Fruit
@wickett #ruggeddevops
@wickett #ruggeddevops
we still don't know
who is attacking us
@wickett #ruggeddevops
We still don't
actually know what
they are attacking
@wickett #ruggeddevops
Real Threats go Unknown
so Developers fix what the
automated tooling detected
at a certain point in time
@wickett #ruggeddevops
Add Application
Security Telemetry
@wickett #ruggeddevops
badidea #4
Put in tooling that no
one outside of security
can understand
@wickett #ruggeddevops
usually in the name
of compliance
@wickett #ruggeddevops
“Get a Web App Firewall
dude!”
- PCI-DSS Req 6.6
@wickett #ruggeddevops
@wickett #ruggeddevops
Choose your own
adventure…
@wickett #ruggeddevops
smallest possible
solution you can
consider a WAF…
@wickett #ruggeddevops
Our CDN added
ModSecurity Ruleset
Huzzah!
@wickett #ruggeddevops
An appliance that
blocks all the things
@wickett #ruggeddevops
And now you wonder
why no one eats lunch
with you anymore
@wickett #ruggeddevops
“every aspect of managing WAFs is an
ongoing process. This is the antithesis
of set it and forget it technology.
That is the real point of this research.
To maximize value from your WAF you
need to go in with everyone’s eyes open
to the effort required to get and keep
the WAF running productively.”
- a whitepaper from a WAF vendor
@wickett #ruggeddevops
@wickett #ruggeddevops
Ok, Security has to change…
How do we add value
already?
@wickett #ruggeddevops
Two ways!
@wickett #ruggeddevops
Add value to Devs
Add value to ops
@wickett #ruggeddevops
Pray that someone
notices
@wickett #ruggeddevops
@wickett #ruggeddevops
Pro-Tip #1
Bad-Behavior Driven Development
(automate those security tools!)
@wickett #ruggeddevops
Start with Adding just one
test for XSS on a few pages
in your app
@wickett #ruggeddevops
@wickett #ruggeddevops
gauntlt is Bad-Behavior
Driven Development
@wickett #ruggeddevops
GAUNTLT
Open source, MIT License

Gauntlt comes with pre-canned steps that hook
security testing tools

Gauntlt does not install tools

Gauntlt wants to be part of the CI/CD pipeline

Be a good citizen of exit status and stdout/stderr
@wickett #ruggeddevops
@wickett #ruggeddevops
@wickett #ruggeddevops
@wickett #ruggeddevops
Be Mean to Your
Code
@wickett #ruggeddevops
Gauntlt Uses Cucumber
and its awesome
@wickett #ruggeddevops
@wickett #ruggeddevops
@wickett #ruggeddevops
here’s an XSS attack
Example
@wickett #ruggeddevops
@slow @final
Feature: Look for cross site scripting (xss) using arachni
against a URL
Scenario: Using arachni, look for cross site scripting and
verify no issues are found
Given "arachni" is installed
And the following profile:
| name | value |
| url | http://localhost:8008 |
When I launch an "arachni" attack with:
"""
arachni --modules=xss --depth=1 --link-count=10 --auto-
redundant=2 <url>
"""
Then the output should contain "0 issues were detected."
@wickett #ruggeddevops
http://theagileadmin.com/2015/06/09/pragmatic-security-and-
rugged-devops/
@wickett #ruggeddevops
github.com/gauntlt/gauntlt-demo
@wickett #ruggeddevops
github.com/gauntlt/gauntlt-starter-kit
@wickett #ruggeddevops
leanpub.com/hands-on-gauntlt
Hands-on Gauntlt
Book
@wickett #ruggeddevops
Pro-tip #2
Put security testing in
your continuous
integration system
@wickett #ruggeddevops
@wickett #ruggeddevops
@wickett #ruggeddevops
https://speakerdeck.com/garethr/battle-tested-code-without-the-battle
@wickett #ruggeddevops
Pro-Tip #3
Add Application Security
telemetry to devs and ops
@wickett #ruggeddevops
Convert App Security
Logs into metrics in the
systems dev and ops use
StatsD
@wickett #ruggeddevops
RunTime Correlation
between biz, ops, dev, sec
@wickett #ruggeddevops
SQLi Attempts + HTTP 500’s
or
login spikes + transaction
decrease
@wickett #ruggeddevops
Runtime
Instrumentation for
Application Security
@wickett #ruggeddevops
Pro-Tip #4
Get hugs from the
auditors and add
Hardening and Audit using
config management
@wickett #ruggeddevops
Open Source
Hardening Framework
chef/puppet/ansible
http://hardening.io/
@wickett #ruggeddevops
Run Nightly Audits of
your Hardening using
Config Management
(Chef audit mode)
https://www.chef.io/blog/2015/04/09/chef-audit-mode-cis-benchmarks/
@wickett #ruggeddevops
OS and Config
Management
@wickett #ruggeddevops
reverse the trend
Add Value to Devs
Add Value to Ops
@wickett #ruggeddevops
Software development is a constant experiment in knowing
Application Security abdicated runtime responsibility and
development responsibility through incoherent
philosophical approaches and fostering silo-thinking
Security now is where Ops was 7 years ago.
Ops found a path to change through devops, security can
too
There are three ways we can add value: at development, at
deploy, at runtime
Summary
@wickett #ruggeddevops
Bad-Behavior Driven Development
Weaponizing your CD Pipeline
Application Security Telemetry and Monitoring
Continuous Hardening and Audit
Have a S-BOM! (Software Bill of Materials)
Practices

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