SlideShare a Scribd company logo
DevOps for 
Defenders 
Ruggedizing the Pipeline
James Wickett 
james@wickett.me 
Austin, TX 
Rugged Dev Podcast 
Gauntlt Core Team 
DevOps Days Austin Organizer 
DevOps Days Global Organizer
My Journey 
Clouding since 2008 and DevOpsing since 2010! 
Led National Instruments R&D Cloud Ops team 
IoT and Cloud products at Mentor Graphics 
Working at Signal Sciences Corp
We’re making AppSec effective and practical 
signalsciences.com
Conclusions 
We optimize for the perceived probable 
Agile, DevOps and Continuous Delivery practices 
have approached this problem in different ways 
InfoSec is behind but has a chance to add value 
Integrating into the build pipeline wins
Humans optimize for 
the probable
We optimize for the 
probable
Happy Path 
Engineering
We optimize for the 
possible
Over Engineering
We optimize for the 
perceived probable
How do we perceive 
what is probable?
How do we know 
anything?
Epistemological Problem 
of Software Development
We attempt to solve it 
by gathering data or 
rhetoric
Approaches to solve 
perceived probable 
problem
Arc 1: Agile
Agile discovered we don’t 
know what we are building
Solution: release features 
to customers rapidly
Just Ship It!
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
Agile Summary 
Rapid Iterations Win
DevOps for Defenders in the Enterprise
Agile eventually births 
DevOps
DevOps for Defenders in the Enterprise
Arc 2: DevOps
Agile Infrastructure 
@littleidea @patrickdebois at Velocity 2009 
http://itrevolution.com/the-history-of-devops/
http://www.slideshare.net/jallspaw/10-deploys-per-day-dev-and-ops-cooperation-at-flickr
First DevOps Days, 
Ghent 2009 
@patrickdebois
DevOps is a 
community movement
http://dev2ops.org/blog/2010/2/22/what-is-devops.html
DevOps realized that 
Ops doesn't know what 
Devs know and vice 
versa
DevOps is an 
epistemological 
breakthrough joining 
disparate people around 
a common problem
Culture
DevOps for Defenders in the Enterprise
Traditional Dev to 
Ops Ratio 
Dev : Ops 
10 : 1
“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
Culture is the most 
important aspect to DevOps 
succeeding in the enterprise
What we value 
determines our culture
DevOps for Defenders in the Enterprise
Culture affects
Mutual Understanding 
Shared Language 
Openness 
Visualization 
Tooling
DevOps for Defenders in the Enterprise
http://puppetlabs.com/sites/default/files/2014-state-of-devops-report.pdf
the first scientific study of the 
relationship between organizational 
performance, IT performance and 
DevOps practices
Firms with 
high-performing IT 
organizations were twice 
as likely to exceed their 
profitability, market share 
and productivity goals.
DevOps practices 
improve IT performance
Organizational culture is one of the 
strongest predictors of both IT 
performance and overall 
performance of 
the organization.
Job satisfaction is the No. 1 
predictor of organizational 
performance.
Culture 
Automation 
Measurement 
Sharing 
@botchagalupe 
@damonedwards
Antipattern: 
Rebrand 
your ops 
team to 
devops team
Culture Influencers 
Decrease time from development to release 
Blameless post-mortems 
Reward failure and have a high emphasis on 
testing 
Unite different disciplines (like dev + ops) to solve 
problems 
http://www.slideshare.net/wickett/the-devops-way-of-delivering-results-in-the-enterprise
Automation
Antipattern: 
Manual 
config of 
production 
environment
Beware of the 
DevOps 
Software 
Solution
Seek automation to 
increase repeatability
A Sample of the 
Automation toolspace 
Chef, Puppet, Ansible, CfEngine 
Rundeck, Mcollective 
Jenkins, Travis, Kitchen 
Cucumber, Gauntlt, ServerSpec 
Vagrant, Docker
Decrease barriers to 
Deploy
Measurement
Old Way: 
CPU, Mem, Avg Load
New Way 
Metrics mapped to stuff 
you actually care about
Business Metrics 
Event Correlation 
Usage based monitoring
Sharing
Dashboards for all to see 
Cultural adjustment 
Deploy Bot
DevOps for Defenders in the Enterprise
Arc 3: Continuous 
Delivery
DevOps for Defenders in the Enterprise
DevOps Deming Style!
Manufacturing Wisdom 
of the 50’s and 60’s
Goldratt 
Deming 
Toyota
Black Belts 
Six Sigma 
Kanban 
Lean
Batch size of 1
Old Way 
Changes break stuff, so 
limit them and batch 
them all together
Change Control Windows 
Roll Backs
New Way 
Delivery of one change at 
a time reduces outages, 
increases performance, 
and limits technical debt
DevOps for Defenders in the Enterprise
DevOps for Defenders in the Enterprise
Anyone can deploy… 
You must deploy your stuff
Continuous Delivery is 
not merely how often 
you deliver but how little 
you can deliver at a time
DevOps for Defenders in the Enterprise
The Next Arc: Security
The Next Arc: Security 
Rugged
“… those stupid 
developers” 
- Security person
“Security prefers a system 
powered off and unplugged” 
- Developer
Cultural unrest with 
security in an organization
Differing priorities
Compliance Driven 
Culture: PCI, SOX, …
“[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”
Ratio Problem 
Devs : Ops : Security 
100 : 10 : 1
DevOps for Defenders in the Enterprise
Security Tools 
are run out-of-band
Security tools are 
confusing
DevOps for Defenders in the Enterprise
and when they are done they 
give you this lovely gem
The tide is changing
Resiliency Engineering
Netflix 
famously 
released 
chaos 
monkey
Rugged
DevOps for Defenders in the Enterprise
The Rugged 
Manifesto
I am rugged and, more importantly, 
my code is rugged. 
I recognize that software has become 
a foundation of our modern world. 
I recognize the awesome 
responsibility that comes with this 
foundational role.
I recognize that my code will be used in 
ways I cannot anticipate, in ways it 
was not designed, and for longer than 
it was ever intended. 
I recognize that my code will be 
attacked by talented and persistent 
adversaries who threaten our physical, 
economic and national security.
I recognize these things – and I 
choose to be rugged. 
I am rugged because I refuse to be a 
source of vulnerability or weakness. 
I am rugged because I assure my 
code will support its mission.
I am rugged because my code can 
face these challenges and persist in 
spite of them. 
I am rugged, not because it is easy, 
but because it is necessary and I 
am up for the challenge.
http://www.slideshare.net/wickett/putting-rugged-into-your-devops-toolchain
Dev / Ops / Sec 
Join forces
The Society of Rugged 
Developers 
ruggeddev.org
DevOps for Defenders in the Enterprise
Rugged Journey 
Quality 
Transparency 
Value Creation 
Culture infusion
#RuggedDevOps
http://www.slideshare.net/wickett/putting-rugged-into-your-devops-toolchain
http://videos.2012.appsecusa.org/video/54250716
http://www.youtube.com/watch?v=jQblKuMuS0Y
https://speakerdeck.com/garethr/security-monitoring-penetration-testing-meets-monitoring
http://vimeo.com/75930344 
https://speakerdeck.com/mkonda/appsecusa-2013-insecure-expectations
Try this at home
Add Security Tooling 
to Delivery Pipeline
…to influence Culture, 
Automation, Measurement 
and Sharing
Security Testing 
Static Code Analysis 
Dynamic Testing 
Virus Scanning 
Code Signing Checks 
Business logic/flow testing
Wouldn’t it be great if we 
could automate our 
security tests…
http://static.hothdwallpaper.net/51b8e4ee5a5ae19808.jpg
Enter Gauntlt
gauntlt.org
Gauntlt Philosophy 
Gauntlt comes with pre-canned steps that hook 
security testing tools 
Gauntlt does not install tools 
Gauntlt can be part of the CI/CD pipeline 
Be a good citizen of exit status and stdout/stderr 
MIT Open Source License
Security + Cucumber = 
Gauntlt
Attack Logic 
GIVEN 
WHEN 
THEN
DevOps for Defenders in the Enterprise
Who uses Gauntlt?
arachni 
nmap 
sqlmap 
sslyze 
dirb 
garmr 
generic
sqli 
xss 
fuzzing 
forceful browsing 
info leaks 
heartbleed 
…
TLDR; 
Gauntlt automates 
security tools
TLDR; 
Gauntlt facilitates 
collaboration
more on gauntlt 
• Google Group > https://groups.google.com/d/ 
forum/gauntlt 
• Wiki > https://github.com/gauntlt/gauntlt/wiki 
• Twitter > @gauntlt 
• IRC > #gauntlt on freenode 
• Issue tracking > http://github.com/gauntlt/gauntlt
Free Gauntlt Book 
request a copy 
book@gauntlt.org 
Caveat Emptor: 
Under 
development! 
Valid until Dec 3rd
Try this at home
Fully functioning 
attacking pipeline
Fork this repo
https://github.com/secure-pipeline/rails-travis-example
Go through the labs 
in ./velocity
DevOps for Defenders in the Enterprise
Conclusions 
We optimize for the perceived probable 
Agile, DevOps and Continuous Delivery practices 
have approached this problem in different ways 
InfoSec is behind but has a chance to add value 
Integrating into the build pipeline wins

More Related Content

PDF
NewOps Days 2019: The New Ways of Chaos, Security, and DevOps
PDF
DevOps for the Discouraged
PDF
DevSecOps and the New Path Forward
PDF
Application Security Epistemology in a Continuous Delivery World
PDF
The New Ways of Chaos, Security, and DevOps
PDF
The Seven Habits of the Highly Effective DevSecOp
PDF
Epistemological Problem of Application Security
PDF
Pragmatic Security and Rugged DevOps - SXSW 2015
NewOps Days 2019: The New Ways of Chaos, Security, and DevOps
DevOps for the Discouraged
DevSecOps and the New Path Forward
Application Security Epistemology in a Continuous Delivery World
The New Ways of Chaos, Security, and DevOps
The Seven Habits of the Highly Effective DevSecOp
Epistemological Problem of Application Security
Pragmatic Security and Rugged DevOps - SXSW 2015

What's hot (19)

PDF
Agile Relevance in the age of Continuous Everything ....
PDF
The Security, DevOps, and Chaos Playbook to Change the World
PPT
2012 Velocity London: DevOps Patterns Distilled
PPTX
2014 State Of DevOps Findings! Velocity Conference
PDF
Teaching Elephants to Dance (and Fly!) A Developer's Journey to Digital Trans...
PPTX
How Can We Better Sell DevOps?
PDF
The Path of DevOps Enlightenment for InfoSec
PDF
STARCANADA 2015: Lightning Strikes the Keynotes
PDF
Outpost24 webinar: Turning DevOps and security into DevSecOps
PDF
PNSQC 2021 January 28 Culture Jam
PPTX
Leading A DevOps Transformation: Lessons Learned
PPTX
ServiceNow ITIL at Ludicrous Speeds - Rugged DevOps
PPTX
State of DevSecOps - DevSecOpsDays 2019
PDF
2013 Velocity DevOps Metrics -- It's Not Just For WebOps Any More!
PDF
DevOps – what is it? Why? Is it real? How to do it?
PPTX
Kim itSMF New England: ITIL at Ludicrous Speeds - Rugged DevOps 6a
PPTX
PuppetConf2012GeneKim
PDF
Optimizing Security Velocity in Your DevSecOps Pipeline at Scale
PPTX
Stranded on Infosec Island: Defending the Enterprise with Nothing but Windows...
Agile Relevance in the age of Continuous Everything ....
The Security, DevOps, and Chaos Playbook to Change the World
2012 Velocity London: DevOps Patterns Distilled
2014 State Of DevOps Findings! Velocity Conference
Teaching Elephants to Dance (and Fly!) A Developer's Journey to Digital Trans...
How Can We Better Sell DevOps?
The Path of DevOps Enlightenment for InfoSec
STARCANADA 2015: Lightning Strikes the Keynotes
Outpost24 webinar: Turning DevOps and security into DevSecOps
PNSQC 2021 January 28 Culture Jam
Leading A DevOps Transformation: Lessons Learned
ServiceNow ITIL at Ludicrous Speeds - Rugged DevOps
State of DevSecOps - DevSecOpsDays 2019
2013 Velocity DevOps Metrics -- It's Not Just For WebOps Any More!
DevOps – what is it? Why? Is it real? How to do it?
Kim itSMF New England: ITIL at Ludicrous Speeds - Rugged DevOps 6a
PuppetConf2012GeneKim
Optimizing Security Velocity in Your DevSecOps Pipeline at Scale
Stranded on Infosec Island: Defending the Enterprise with Nothing but Windows...
Ad

Viewers also liked (19)

PDF
How to Effect Change in the Epistemological Wasteland of Application Security
PDF
Be Mean To Your Code: Rugged Development & You
PPTX
Building your All-Star DevOps Team – "Planning, Process and Partners"
PDF
Jan de Vries - How to convince your boss that it is DevOps that he wants
PDF
Long live the DevOps team - LeedsDevOps - 2015-10-22 - Matthew Skelton
PDF
DevOps Proverbs - DevOps Wisdom, Principles and Practices
PPTX
DevOps & the Dark Side 10 ways to convince your team DevOps is a force for good
PDF
Serverless Security: Doing Security in 100 milliseconds
ODP
Building A devopsy Team
PPTX
Ignite: When You Need A DevOps Team
PPTX
Testing in a DevOps team
PPTX
Why to docker
PDF
Shirt Ops: How to make awesome t-shirts for your conference
PDF
PPTX
Education Disrupted: 11 Trends That Are Changing Education Forever
PDF
AWilson_finalunit_12-9-13 CTI
PDF
Avto0232
PDF
Improv Content Strategy: Doing Things the Wrong Way, the Right Way
PPTX
Estonia and European Debt Crisis
How to Effect Change in the Epistemological Wasteland of Application Security
Be Mean To Your Code: Rugged Development & You
Building your All-Star DevOps Team – "Planning, Process and Partners"
Jan de Vries - How to convince your boss that it is DevOps that he wants
Long live the DevOps team - LeedsDevOps - 2015-10-22 - Matthew Skelton
DevOps Proverbs - DevOps Wisdom, Principles and Practices
DevOps & the Dark Side 10 ways to convince your team DevOps is a force for good
Serverless Security: Doing Security in 100 milliseconds
Building A devopsy Team
Ignite: When You Need A DevOps Team
Testing in a DevOps team
Why to docker
Shirt Ops: How to make awesome t-shirts for your conference
Education Disrupted: 11 Trends That Are Changing Education Forever
AWilson_finalunit_12-9-13 CTI
Avto0232
Improv Content Strategy: Doing Things the Wrong Way, the Right Way
Estonia and European Debt Crisis
Ad

Similar to DevOps for Defenders in the Enterprise (20)

PDF
Rugged DevOps (eBook): 10 Ways to Start Embedding Security into DevOps Patterns
PDF
Pragmatic Pipeline Security
PDF
The Emergent Cloud Security Toolchain for CI/CD
PDF
The DevSecOps Builder’s Guide to the CI/CD Pipeline
PDF
DevOps Beyond the Buzzwords: What it Means to Embrace the DevOps Lifestyle
PDF
DevSecOps and the CI/CD Pipeline
PPTX
Security & DevOps- Ways To Make Sure Your Apps & Infrastructure Are Secure
PDF
Devops, Secops, Opsec, DevSec *ops *.* ?
PDF
AgileDC15 I'm Using Chef So I'm DevOps Right?
PPTX
You Build It, You Secure It: Introduction to DevSecOps
PPTX
JavaOne 2015 Devops and the Darkside CON6447
PPTX
DevSecOps - It can change your life (cycle)
ODP
Lessons from DevOps: Taking DevOps practices into your AppSec Life
PPTX
Succeeding-Marriage-Cybersecurity-DevOps final
PPTX
Achieving Secure DevOps: Overcoming the Risks of Modern Service Delivery
PDF
The What, Why, and How of DevSecOps
PDF
Codifying Devops by Gourav Shah
PDF
Dev ops lessons learned - Michael Collins
PDF
Intro to DevOps
PPTX
One Does Not Simply Walk Into Devops
Rugged DevOps (eBook): 10 Ways to Start Embedding Security into DevOps Patterns
Pragmatic Pipeline Security
The Emergent Cloud Security Toolchain for CI/CD
The DevSecOps Builder’s Guide to the CI/CD Pipeline
DevOps Beyond the Buzzwords: What it Means to Embrace the DevOps Lifestyle
DevSecOps and the CI/CD Pipeline
Security & DevOps- Ways To Make Sure Your Apps & Infrastructure Are Secure
Devops, Secops, Opsec, DevSec *ops *.* ?
AgileDC15 I'm Using Chef So I'm DevOps Right?
You Build It, You Secure It: Introduction to DevSecOps
JavaOne 2015 Devops and the Darkside CON6447
DevSecOps - It can change your life (cycle)
Lessons from DevOps: Taking DevOps practices into your AppSec Life
Succeeding-Marriage-Cybersecurity-DevOps final
Achieving Secure DevOps: Overcoming the Risks of Modern Service Delivery
The What, Why, and How of DevSecOps
Codifying Devops by Gourav Shah
Dev ops lessons learned - Michael Collins
Intro to DevOps
One Does Not Simply Walk Into Devops

More from James Wickett (20)

PDF
A Pragmatic Union: Security and SRE
PDF
A Way to Think about DevSecOps: MEASURE
PDF
A Tale of Woe, Chaos, and Business
PDF
A DevSecOps Tale of Business, Engineering, and People
PDF
The New Ways of DevSecOps - The Secure Dev 2019
PDF
DevOpsDays Austin: Security in the FaaS Lane
PDF
Serverless Security: A How-to Guide @ SnowFROC 2019
PDF
Release Your Inner DevSecOp
PDF
Security in the FaaS Lane
PDF
The New Security Playbook: DevSecOps
PDF
Adversary Driven Defense in the Real World
PDF
The State of DevSecOps in 2018
PDF
DevSecOps in the Year 2018
PDF
The Emergent Cloud Security Toolchain for CI/CD
PDF
AppSec California 2018: The Path of DevOps Enlightenment for InfoSec
PDF
LambHack: A Vulnerable Serverless Application
PDF
Defense-Oriented DevOps for Modern Software Development
PDF
Innotech Austin 2017: The Path of DevOps Enlightenment for InfoSec
PDF
Serverless Security at LASCON 2017
PDF
The Path of DevOps Enlightenment for InfoSec
A Pragmatic Union: Security and SRE
A Way to Think about DevSecOps: MEASURE
A Tale of Woe, Chaos, and Business
A DevSecOps Tale of Business, Engineering, and People
The New Ways of DevSecOps - The Secure Dev 2019
DevOpsDays Austin: Security in the FaaS Lane
Serverless Security: A How-to Guide @ SnowFROC 2019
Release Your Inner DevSecOp
Security in the FaaS Lane
The New Security Playbook: DevSecOps
Adversary Driven Defense in the Real World
The State of DevSecOps in 2018
DevSecOps in the Year 2018
The Emergent Cloud Security Toolchain for CI/CD
AppSec California 2018: The Path of DevOps Enlightenment for InfoSec
LambHack: A Vulnerable Serverless Application
Defense-Oriented DevOps for Modern Software Development
Innotech Austin 2017: The Path of DevOps Enlightenment for InfoSec
Serverless Security at LASCON 2017
The Path of DevOps Enlightenment for InfoSec

Recently uploaded (20)

PDF
Review of recent advances in non-invasive hemoglobin estimation
PDF
Machine learning based COVID-19 study performance prediction
PDF
7 ChatGPT Prompts to Help You Define Your Ideal Customer Profile.pdf
PDF
Agricultural_Statistics_at_a_Glance_2022_0.pdf
PPTX
A Presentation on Artificial Intelligence
PDF
Bridging biosciences and deep learning for revolutionary discoveries: a compr...
PPTX
Understanding_Digital_Forensics_Presentation.pptx
PDF
Dropbox Q2 2025 Financial Results & Investor Presentation
PDF
Per capita expenditure prediction using model stacking based on satellite ima...
PPTX
Effective Security Operations Center (SOC) A Modern, Strategic, and Threat-In...
PDF
Approach and Philosophy of On baking technology
PDF
Empathic Computing: Creating Shared Understanding
PDF
Peak of Data & AI Encore- AI for Metadata and Smarter Workflows
PDF
CIFDAQ's Market Insight: SEC Turns Pro Crypto
PDF
Blue Purple Modern Animated Computer Science Presentation.pdf.pdf
PDF
Spectral efficient network and resource selection model in 5G networks
PDF
Unlocking AI with Model Context Protocol (MCP)
PDF
Encapsulation_ Review paper, used for researhc scholars
PPTX
Big Data Technologies - Introduction.pptx
PDF
Reach Out and Touch Someone: Haptics and Empathic Computing
Review of recent advances in non-invasive hemoglobin estimation
Machine learning based COVID-19 study performance prediction
7 ChatGPT Prompts to Help You Define Your Ideal Customer Profile.pdf
Agricultural_Statistics_at_a_Glance_2022_0.pdf
A Presentation on Artificial Intelligence
Bridging biosciences and deep learning for revolutionary discoveries: a compr...
Understanding_Digital_Forensics_Presentation.pptx
Dropbox Q2 2025 Financial Results & Investor Presentation
Per capita expenditure prediction using model stacking based on satellite ima...
Effective Security Operations Center (SOC) A Modern, Strategic, and Threat-In...
Approach and Philosophy of On baking technology
Empathic Computing: Creating Shared Understanding
Peak of Data & AI Encore- AI for Metadata and Smarter Workflows
CIFDAQ's Market Insight: SEC Turns Pro Crypto
Blue Purple Modern Animated Computer Science Presentation.pdf.pdf
Spectral efficient network and resource selection model in 5G networks
Unlocking AI with Model Context Protocol (MCP)
Encapsulation_ Review paper, used for researhc scholars
Big Data Technologies - Introduction.pptx
Reach Out and Touch Someone: Haptics and Empathic Computing

DevOps for Defenders in the Enterprise