AppSec California 2018: The Path of DevOps Enlightenment for InfoSec

@WICKETT
The Path of DevOps
Enlightenment for InfoSec
JAMES WICKETT || SIGNAL SCIENCES

@WICKETT
Want the slides and
referenced links?
james@signalsciences.com

@WICKETT
‣ HEAD OF RESEARCH AT SIGNAL SCIENCES
‣ ORGANIZER OF DEVOPS DAYS AUSTIN
‣ LYNDA.COM AUTHOR ON DEVOPS
‣ BLOG AT THEAGILEADMIN.COM
@WICKETT

@WICKETT
‣ DEVOPS IS CHANGING AND THERE IS A BIG RISK
TO LOSE OUR WAY.
‣ SECURITY IS IN CRISIS
‣ SECURITY AT FORWARD-LEANING SHOPS HAVE
FOUND THE NEW WAY.
‣ LET’S JUXTAPOSE THE OLD WAY AND THE NEW
WAY OF SECURITY IN DEVOPS.
SUMMARY

@WICKETT
‣ CAN SECURITY AS AN INDUSTRY RISE TO THE
DEMANDS OF DEVOPS?
‣ IS THE DEVOPS CULTURE ABLE TO HANDLE
SECURITY AND ALL OF OUR BAGGAGE?
‣ WILL SECURITY DESTROY THE DEVOPS
CULTURE?
QUESTIONS ON MY MIND

@WICKETT
‣ WEB AND ECOMM FOR $1B COMPANY
‣ BRUTAL ONCALL ROTATIONS
‣ +24HR DEPLOYMENTS
‣ WATERFALL, WATERFALL, WATERFALL
‣ FRIENDS ARE BORN FROM ADVERSITY
FIRST BIGCO JOB

@WICKETT
‣ IN 2007 WENT STARTUP AND AWS CLOUD
‣ LEARNED A BIT ABOUT FAILURE AND
HAPPINESS
‣ REJOINED OLD TEAM IN 2010 FOR NEW CLOUD
VENTURE BACK IN BIGCO
CLOUDING FOR PROFIT

@WICKETT
‣ DEVOPS AND INFRA AS CODE
‣ NOT CD, BUT DEPLOYS DAILY
‣ AT BIGCO DELIVERED 4 SAAS PRODUCTS IN 2
YEARS WITH DEVOPS AND CLOUD
ENTER DEVOPS

@WICKETT
‣ FOUND RUGGED SOFTWARE
‣ MET GENE KIM IN 2012 IN A BAR IN AUSTIN
‣ CREATED GAUNTLT
‣ LATER, JOINED SIGNAL SCIENCES
DEVOPS AND SECURITY

@WICKETT
Labor Inequity
Permeates IT Ranks

@WICKETT
Yet, I remained optimistic
for DevOps+Security

@WICKETT
‣ DEVOPS ON A BUS AT RSA (SECURITY BEING
SECURITY)
‣ EXPO FLOOR AT DOCKER CON AND THE
DEVOPS TOOLCHAIN (OPERATIONS BEING
OPERATIONS)
TWO EVENTS

@WICKETT
HAD WE ALLOWED DEVOPS TO BE
A NEW GIMMICK OR SLOGAN ?

@WICKETT
WHAT HAD DEVOPS BECOME?

@WICKETT
OUR ROOTS: FRIENDSHIP

@WICKETT
There is irony in my
story…

@WICKETT
‣ TEACH THREE DEVOPS CLASSES IN THE DEVOPS
FOUNDATIONS SERIES AT LYNDA / LINKEDIN
LEARNING
‣ WORK AT A POPULAR VENDOR OF DEVSECOPS
SOLUTIONS
‣ WRITE DEVOPS AND SECURITY ARTICLES AS
PART OF MY ROLE AT SIGNAL SCIENCES

@WICKETT
CULTURE IS THE MOST
IMPORTANT ASPECT TO DEVOPS
SUCCEEDING IN THE
ENTERPRISE
- PATRICK DEBOIS

@WICKETT
‣ MUTUAL UNDERSTANDING
‣ SHARED LANGUAGE
‣ SHARED VIEWS
‣ COLLABORATIVE TOOLING
4 KEYS TO CULTURE

@WICKETT
Make a connection and
friend through your
journey today

@WICKETT
Security is in Crisis

@WICKETT
Companies are spending a great deal on
security, but we read of massive computer-
related attacks. Clearly something is wrong.
The root of the problem is twofold:
we’re protecting the wrong things,
and we’re hurting productivity in the process.
THINKING SECURITY, STEVEN M. BELLOVIN 2015

@WICKETT
[Security by 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
Security is often the
cultural outlier in an
organization

@WICKETT
many security teams work
with a worldview where their
goal is to inhibit change as
much as possible

@WICKETT
“SECURITY PREFERS A SYSTEM POWERED
OFF AND UNPLUGGED”
- DEVELOPER

@WICKETT
“…THOSE STUPID DEVELOPERS”
- SECURITY PERSON

@WICKETT
It is 30 times cheaper to
ﬁx security defects in dev
vs. Prod
NIST, 2002, The Economic Impacts of Inadequate Infra for Software Testing

@WICKETT
Security must
Change or Die

@WICKETT
“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.”
- WHITEPAPER FROM AN UNDISCLOSED WAF VENDOR

@WICKETT
THE AVERAGE TIME TO DELIVER CORPORATE IT PROJECTS
HAS INCREASED FROM ~8.5 MONTHS TO OVER 10
MONTHS IN THE LAST 5 YEARS
Revving up your Corporate RPMs, Fortune Magazine, Feb 1, 2016
THE GROWTH OF [SECURITY] FUNCTIONS WHICH IS TOO
OFTEN POORLY COORDINATED… [RESULTING IN] A
PROLIFERATION OF NEW TASKS IN THE AREAS OF
COMPLIANCE, PRIVACY AND DATA PROTECTION.

@WICKETT
Many security professionals
have a hard time adapting their
existing practices to a world
where requirements can change
every few weeks, or where they
are never written down at all.

@WICKETT
Security didn’t get an
invite to the DevOps
party!
- John Willis (@botchagalupe)
“You Build It, You Secure It” DOES 2017

@WICKETT
Read-only containers and
serverless shift the
security story to almost
100% application security

@WICKETT
DevOps
A New Traveling Companion
for Security
(…and probably the only way to survive)

@WICKETT
High performers spend 50 percent less
time remediating security issues than
low performers.
By better integrating information security
objectives into daily work, teams achieve
higher levels of IT performance and build
more secure systems.
2016 State of DevOps Report

@WICKETT
High performing orgs achieve
quality by incorporating
security (and security teams)
into the delivery process
2016 State of DevOps Report

@WICKETT
http://www.youtube.com/watch?v=jQblKuMuS0Y

@WICKETT
OLD PATH VS. NEW PATH
Embrace Secrecy Create Feedback Loops
Just Pass Audit! Compliance adds Value
Enforce Stability Create Chaos
Build a Wall Zero Trust Networks
Slow Validation Fast and Non-blocking
Certainty Testing Adversity Testing
Test when Done Shift Left
Process Driven The Paved Road

@WICKETT
A security team who embraces
openness about what it does and
why, spreads understanding.
- Rich Smith

@WICKETT
Runtime is arguably the
most important place to
create feedback loops

@WICKETT
‣ ACCOUNT TAKEOVER ATTEMPTS
‣ AREAS OF THE SITE UNDER ATTACK
‣ MOST LIKELY VECTORS OF ATTACK
‣ BUSINESS LOGIC FLOWS
DETECT WHAT MATTERS

@WICKETT
Are you under attack?

@WICKETT
Which is a better feedback loop?
Source: Zane Lackey, Signal Sciences

@WICKETT
Web and AppSec Options:
RASP, NGWAF or Web
Protection Platform

@WICKETT
‣ SURFACE LEVEL
‣ WHAT WENT WRONG? HOW DID IT BREAK?
HOW DO WE FIX IT?
‣ DEEPER LEVEL
‣ WHAT ARE THINGS THAT WENT INTO MAKING
IT NOT AS BAD AS IT COULD HAVE BEEN?
OPERATIONAL TRUTH:
ALL INCIDENTS CAN BE WORSE
Source: John Allspaw, DOES 2017

@WICKETT
‣ POLICIES AND PROCEDURES IN PLACE
‣ EFFECTIVE EXECUTION OF THOSE POLICIES TO
ALLOW YOU TO KEEP FUNCTIONING
‣ MOST OF PCI AND OTHER FRAMEWORKS
PROVIDE REASONABLY GOOD PRACTICES *IF*
YOU REMOVE ALL THE WATERFALL BITS
UNDERSTAND AUDITORS

@WICKETT
[Deploys] can be treated as
standard or routine changes
that have been pre-approved
by management, and that
don’t require a heavyweight
change review meeting.

Separation of Duties Considered Harmful

@WICKETT
In environments where one individual
performs multiple roles (for example,
administration and security operations), duties
may be assigned such that no single
individual has end-to-end control of a process
without an independent checkpoint.
(aka Auditable Delivery Pipeline)

@WICKETT
Developers with Access to
Production, Oh My!!!
https://www.schellmanco.com/blog/2012/12/auditing-devops-
developers-with-access-to-production/

@WICKETT
Check out DevOps Audit
Defense Toolkit
https://cdn2.hubspot.net/hubfs/228391/Corporate/
DevOps_Audit_Defense_Toolkit_v1.0.pdf

@WICKETT
‣ ADD IN CHAOS TO YOUR SYSTEM AND
APPLICATION
‣ CHAOS MONKEY
‣ ANTI-FRAGILE
‣ RELEASE IT! BOOK
CHAOS ENGINEERING

@WICKETT
‣ ADDS MISCONFIG TO THE STACK AND CHECKS
TO SEE IF IT GETS DETECTED
‣ NEW OPEN SOURCE TOOL!
‣ RUNS AS A LAMBDA
CHAOS SLINGR

@WICKETT
‣ VALIDATE YOUR SYSTEM CAN HANDLE CHAOS
THROUGH THE USE OF CHAOS EXPERIMENTS
‣ MANUAL OPT-OUT OF CHAOS
‣ ENGINEERING CULTURE THAT SECURITY CAN
ADOPT
‣ MICHAEL NYGARD’S RELEASE IT (2ND EDITION)
CHAOS EXPERIMENTS

@WICKETT
‣ I AM BEING PEN TESTED ANYWAY, WHY NOT
FIND OUT WHAT THEY ARE FINDING?
‣ 24/7 PEN TESTING
‣ BUILDS DEVELOPER CONFIDENCE
‣ FINDS MIX OF LOW HANGING FRUIT AND
SOMETIMES MUCH MORE!
BUG BOUNTIES

@WICKETT
The ACL is moved from
Network Layer to the
Application Layer

@WICKETT
‣ NO PERIMETER SECURITY
‣ ASSUME COMPROMISE
‣ INSTRUMENT ALL LAYERS
‣ EXTENDS FROM LAPTOPS TO WEB
APPS TO CUSTOMER ACCOUNTS
ZERO TRUST NETWORKS

@WICKETT
Join Wendy Nather
Modern Security Series
Feb 1, Thurs, 12p PST
https://info.signalsciences.com/mfa-multi-factor-authentication-modern-security-series

@WICKETT
‣ DON’T SLOW DELIVERY
‣ CONTINUOUS TESTING AND VALIDATION
‣ TESTING ON THE SIDE OF THE PIPELINE
‣ PENETRATION TESTING OUTSIDE OF DELIVERY
FAST AND NON-BLOCKING

@WICKETT
Currently, at Signal
Sciences we do about 15
deploys per day

@WICKETT
Roughly 10,000 deploys in
the last 2.5 yrs

@WICKETT
CD is how little you can
deploy at a time

@WICKETT
We optimized for cycle
time—the time from code
commit to production

Gave power to the team to deploy

@WICKETT
Signal Sciences is a
software as a service
company and a security
company

@WICKETT
Security is part of CI/CD
and the overall delivery
pipeline

@WICKETT
‣DESIGN
‣INHERIT
‣BUILD
‣DEPLOY
‣OPERATE
PIPELINE PHASES

@WICKETT
‣INHERIT
‣BUILD
‣OPERATE
SECURITY
CONSIDERATIONS
What have I bundled into my
app that leaves me
vulnerable?
Do my build acceptance
tests and integration tests
catch security issues before
release?
Am I being attacked right
now? Is it working?

@WICKETT
The goal should be to come up with a
set of automated tests that probe and
check security configurations and
runtime system behavior for security
features that will execute every time
the system is built and every time it is
deployed.

@WICKETT
Security tools are
intractably noisy and
diﬃcult to use

@WICKETT
A method of collaboration
was needed for devs, ops
and security eng.

@WICKETT
There needed to be a new
language to span the
parties

@WICKETT
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
$ gem install gauntlt
# download example attacks from github
# customize the example attacks
# now you can run gauntlt
$ gauntlt

@WICKETT
@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 —check=xss* <url>
"""
Then the output should contain "0 issues were detected."
Given
When
Then
What?

@WICKETT
“We have saved millions of
dollars using Gauntlt for the
largest healthcare industry
project.”
- Aaron Rinehart, UnitedHealthCare

@WICKETT
http://bit.ly/2s8P1Ll

@WICKETT
‣ 8 LABS FOR GAUNTLT
‣ HOW TO USE GAUNTLT FOR NETWORK CHECKS
‣ GAUNTLT FOR XSS, SQLI, OTHER APSES
‣ HANDLING REPORTING
‣ USING ENV VARS
‣ CI SYSTEM SETUP
WORKSHOP INCLUDES:

@WICKETT
github.com/gauntlt/gauntlt-demo

@WICKETT
github.com/gauntlt/gauntlt-starter-kit

@WICKETT
SOURCE: THE
THREE WAYS OF
DEVOPS, GENE KIM

@WICKETT
Advice: Use Gauntlt in a
docker container

@WICKETT
https://github.com/
gauntlt/gauntlt-docker

@WICKETT
Shifting testing left with
Red Team Mondays
at Intuit

@WICKETT
Inheritance ﬂaws are in
containers too.

@WICKETT
OVER 30% OF OFFICIAL IMAGES IN
DOCKER HUB CONTAIN HIGH PRIORITY
SECURITY VULNERABILITIES
https://banyanops.com/blog/analyzing-docker-hub/

@WICKETT
‣ MAKE IT EASY FOR PEOPLE TO DO THE RIGHT
THING
‣ JASON CHAN, NETFLIX
‣ GOLD IMAGES
‣ BLESSED BUILDS AND DEPENDENCIES
THE PAVED ROAD

@WICKETT
Don’t be a blocker, be an
enabler of the business

AppSec California 2018: The Path of DevOps Enlightenment for InfoSec

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AppSec California 2018: The Path of DevOps Enlightenment for InfoSec