DevSecOps Fundamentals
And Scars to Prove It
I am Matt Tesauro
I think Dev(App)SecOps needs to change and
I’m going to tell you how I see it changing
matt.tesauro@10Security.com / @matt_tesauro
2
Who is this guy?
✖ Reformed programmer and AppSec Engineer
✖ 11+ years in the OWASP community
○ OWASP AppSec Pipeline
○ OWASP DefectDojo
○ OWASP WTE
✖ 20+ years using Floss and Linux
✖ Currently a Go language fanboy
✖ Ee Dan in Tang Soo Do Mi Guk Kwan
(2nd degree black belt)
3
The money shot
4
Not everything
about completing
a goal is sunshine
and roses...
The Anti-money shot
5
Traditional AppSec
Where all this started not so long ago
6
Traditional AppSec
Where all this started not so long ago
7
Security
What Traditional Tooling feels like:
8
9
Let’s be honest for a minute...
10
11
12
The purpose of an
AppSec program is to
evaluate the security
status of the suite of
apps for a business
Basically, to provide a
map to guide business
decisions.
Do you have a full view of
your Application landscape?
13
There’s one more thing
DevSecOps should do...
14
15
Provide a clear and direct path for teams to follow
DevSecOps Concepts
What you should have in mind going forward
16
17
#1 Drive Down Complexity
VS
18
#2 Dependency Management
Balance what you
rely on vs what you
interact with -
things disappear...
19
#3 Shared Clear Understanding
How many assumptions
are hiding in your
whiteboards?
whiteboard != design
whiteboard != shared
understanding
20
#4 Default Security Controls to On
There’s a reason you
have to turn OFF
airbags
Caddy server +
Let’s Encrypt
21
#5 Utilize Frameworks Fully
Do you really
KNOW the
framework
you’re using
and the
security
features it has?
22
#6 Embrace 12 Factor Apps
Cloud-Native before Cloud-Native was cool
23
#7 Codify & Checklist-ify your processes
Makes work:
● Easy to
repeat
● Consistent
● Future
Automation
Friendly
FAF™
24
#8 Servers like Cattle not Pets
25
#8a Servers like Cattle not Pets
Kleenex Handkerchiefs
26
#9 Explode Your Processes
Break existing work into pieces
● Think EAR™
○ Event
○ Action (function)
○ Result / Inform (chatops?)
● Pick a checklist item &
automate (repeat until done)
● Pre-Compute Future Security
Work
DevSecOps Automation
What are the key things to be aware of
27
W Edward DemIng
Spending time
optimizing
anything other than
the critical resource
is an illusion
28
Your people are the
critical resource
29
There’s never enough people or time...
✖ AppSec team size is small vs Dev team
✖ Automate all those things that don’t take
a human brain
✖ DefectDojo (and the rest API) is the heart
of your automation efforts - your single
source of truth
OWASP DefectDojo
An open-source application vulnerability
correlation and security orchestration tool.
The source of truth for a security program that
manages to make vulnerability management work
✖ Consolidating and dedup’ing findings
○ 68+ different tools supported
✖ Maintain product and app info/metadata
✖ Push findingst to defect trackers
✖ Automation with a REST API
31
The “Three Ways of DevOps”
1. Workflow
“Look at your purpose and those processes which aid it”
2. Improve Feedback
“Open yourself to upstream & downstream info”
3. Continual Experimentation and Learning
“Create a culture of innovation and experimentation”
32
AppSec Personnelle
They are the critical resource so
optimize their work
✖ Automate the non-human brain things
✖ Drive up consistency
✖ Increase tracking of work status
✖ Increase flow through the system
✖ Increase visibility and metrics
✖ Reduce any friction with dev teams
33
Security
34
Talk to your constituency
in the language
that THEY speak,
not the one you speak.
As as exercise for the student
35
AppSec Pipelines
Why let dev teams own all the good ideas
36
What’s this AppSec pipeline all about?
✖ Better visibility into WIP
✖ Better understand/track/optimize flow of
DevSecOps work
✖ Significant increase in consistency
○ Each step has a well defined interface
✖ Understanding the cost of switching
✖ Flexible enough for a range of skills &
program maturity
38
Gen 1 AppSec Pipelines
Look at your team’s purpose and
those processes which aid it
39
Real-World AppSec Pipeline example
42
Get your house in order
Gen 2 AppSec Pipelines
Look outside team’s purpose and
those processes which aid it
43
Integrate with DevOpsTeams
DevOps Pipeline AppSec Pipeline
Drop tool(s)
into their
pipeline
Gen 3 AppSec Pipelines
Scale your teams reach and
dramatically increase
speed and visibility
45
✖ A way to conduct automated testing
✖ Run by the AppSec team to
○ Provide visibility of software posture
○ Provide findings to the dev teams
✖ Means to scale Security team coverage
○ No in-depth testing, breadth
○ Pre-calculate testing
✖ Creates a security baseline
46
What does a Gen3 AppSec Pipeline get me?
✖ The one thing that will fix all your problems
✖ A gate that blocks deploys
(especially at first)
✖ Pipeline create artifacts
○ CI/CD => deployed apps
○ AppSec Pipelines =>
Security Findings
47
What an AppSec Pipeline isn’t
48
First get the Cake then do the icing
50
So why should you build an
AppSec Pipeline?
Another
Real-World
AppSec Pipeline
52
AppSec Pipeline Stats
15 Repos
4 Months
5,100 Runs
25,000+
Container Executions
Remember me?
2014 2015 2016
Number of
Assessments 44 224 414
Headcount N/A -3.5 -2
Percentage
Increase N/A 450% 107%
54
55
840.91%
Percentage Increase
56
57
58
DevSecOps can help push visibility north
Visibility
59
Thanks!
Any questions?
You can find me at:
@matt_tesauro
matt.tesauro@10Security.com
60
61
REferences
● Confused panda: https://openclipart.org/detail/69289/confusedpanda
● Jousting Snails - a random twitter post I lost the URL for, sorry
● Map image: https://openclipart.org/detail/823/two-harbours-map
● Gandoff “Shall pass”:
https://shirt.woot.com/offers/halfling-height-requirement
● Pixie dust:
http://www.disneyeveryday.com/bottle-of-tinker-bells-pixie-dust-neck
lace/
● Iceberg of Ignorance:
https://corporate-rebels.com/iceberg-of-ignorance/

DevSecOps Fundamentals and the Scars to Prove it.

  • 1.
  • 2.
    I am MattTesauro I think Dev(App)SecOps needs to change and I’m going to tell you how I see it changing matt.tesauro@10Security.com / @matt_tesauro 2
  • 3.
    Who is thisguy? ✖ Reformed programmer and AppSec Engineer ✖ 11+ years in the OWASP community ○ OWASP AppSec Pipeline ○ OWASP DefectDojo ○ OWASP WTE ✖ 20+ years using Floss and Linux ✖ Currently a Go language fanboy ✖ Ee Dan in Tang Soo Do Mi Guk Kwan (2nd degree black belt) 3
  • 4.
  • 5.
    Not everything about completing agoal is sunshine and roses... The Anti-money shot 5
  • 6.
    Traditional AppSec Where allthis started not so long ago 6
  • 7.
    Traditional AppSec Where allthis started not so long ago 7 Security
  • 8.
  • 9.
  • 10.
    Let’s be honestfor a minute... 10
  • 11.
  • 12.
    12 The purpose ofan AppSec program is to evaluate the security status of the suite of apps for a business Basically, to provide a map to guide business decisions.
  • 13.
    Do you havea full view of your Application landscape? 13
  • 14.
    There’s one morething DevSecOps should do... 14
  • 15.
    15 Provide a clearand direct path for teams to follow
  • 16.
    DevSecOps Concepts What youshould have in mind going forward 16
  • 17.
    17 #1 Drive DownComplexity VS
  • 18.
    18 #2 Dependency Management Balancewhat you rely on vs what you interact with - things disappear...
  • 19.
    19 #3 Shared ClearUnderstanding How many assumptions are hiding in your whiteboards? whiteboard != design whiteboard != shared understanding
  • 20.
    20 #4 Default SecurityControls to On There’s a reason you have to turn OFF airbags Caddy server + Let’s Encrypt
  • 21.
    21 #5 Utilize FrameworksFully Do you really KNOW the framework you’re using and the security features it has?
  • 22.
    22 #6 Embrace 12Factor Apps Cloud-Native before Cloud-Native was cool
  • 23.
    23 #7 Codify &Checklist-ify your processes Makes work: ● Easy to repeat ● Consistent ● Future Automation Friendly FAF™
  • 24.
    24 #8 Servers likeCattle not Pets
  • 25.
    25 #8a Servers likeCattle not Pets Kleenex Handkerchiefs
  • 26.
    26 #9 Explode YourProcesses Break existing work into pieces ● Think EAR™ ○ Event ○ Action (function) ○ Result / Inform (chatops?) ● Pick a checklist item & automate (repeat until done) ● Pre-Compute Future Security Work
  • 27.
    DevSecOps Automation What arethe key things to be aware of 27
  • 28.
    W Edward DemIng Spendingtime optimizing anything other than the critical resource is an illusion 28
  • 29.
    Your people arethe critical resource 29
  • 30.
    There’s never enoughpeople or time... ✖ AppSec team size is small vs Dev team ✖ Automate all those things that don’t take a human brain ✖ DefectDojo (and the rest API) is the heart of your automation efforts - your single source of truth
  • 31.
    OWASP DefectDojo An open-sourceapplication vulnerability correlation and security orchestration tool. The source of truth for a security program that manages to make vulnerability management work ✖ Consolidating and dedup’ing findings ○ 68+ different tools supported ✖ Maintain product and app info/metadata ✖ Push findingst to defect trackers ✖ Automation with a REST API 31
  • 32.
    The “Three Waysof DevOps” 1. Workflow “Look at your purpose and those processes which aid it” 2. Improve Feedback “Open yourself to upstream & downstream info” 3. Continual Experimentation and Learning “Create a culture of innovation and experimentation” 32
  • 33.
    AppSec Personnelle They arethe critical resource so optimize their work ✖ Automate the non-human brain things ✖ Drive up consistency ✖ Increase tracking of work status ✖ Increase flow through the system ✖ Increase visibility and metrics ✖ Reduce any friction with dev teams 33 Security
  • 34.
    34 Talk to yourconstituency in the language that THEY speak, not the one you speak.
  • 35.
    As as exercisefor the student 35
  • 36.
    AppSec Pipelines Why letdev teams own all the good ideas 36
  • 38.
    What’s this AppSecpipeline all about? ✖ Better visibility into WIP ✖ Better understand/track/optimize flow of DevSecOps work ✖ Significant increase in consistency ○ Each step has a well defined interface ✖ Understanding the cost of switching ✖ Flexible enough for a range of skills & program maturity 38
  • 39.
    Gen 1 AppSecPipelines Look at your team’s purpose and those processes which aid it 39
  • 41.
  • 42.
  • 43.
    Gen 2 AppSecPipelines Look outside team’s purpose and those processes which aid it 43
  • 44.
    Integrate with DevOpsTeams DevOpsPipeline AppSec Pipeline Drop tool(s) into their pipeline
  • 45.
    Gen 3 AppSecPipelines Scale your teams reach and dramatically increase speed and visibility 45
  • 46.
    ✖ A wayto conduct automated testing ✖ Run by the AppSec team to ○ Provide visibility of software posture ○ Provide findings to the dev teams ✖ Means to scale Security team coverage ○ No in-depth testing, breadth ○ Pre-calculate testing ✖ Creates a security baseline 46 What does a Gen3 AppSec Pipeline get me?
  • 47.
    ✖ The onething that will fix all your problems ✖ A gate that blocks deploys (especially at first) ✖ Pipeline create artifacts ○ CI/CD => deployed apps ○ AppSec Pipelines => Security Findings 47 What an AppSec Pipeline isn’t
  • 48.
    48 First get theCake then do the icing
  • 50.
    50 So why shouldyou build an AppSec Pipeline?
  • 51.
  • 52.
    52 AppSec Pipeline Stats 15Repos 4 Months 5,100 Runs 25,000+ Container Executions
  • 53.
  • 54.
    2014 2015 2016 Numberof Assessments 44 224 414 Headcount N/A -3.5 -2 Percentage Increase N/A 450% 107% 54
  • 55.
  • 56.
  • 57.
  • 58.
    58 DevSecOps can helppush visibility north Visibility
  • 59.
  • 60.
    Thanks! Any questions? You canfind me at: @matt_tesauro matt.tesauro@10Security.com 60
  • 61.
    61 REferences ● Confused panda:https://openclipart.org/detail/69289/confusedpanda ● Jousting Snails - a random twitter post I lost the URL for, sorry ● Map image: https://openclipart.org/detail/823/two-harbours-map ● Gandoff “Shall pass”: https://shirt.woot.com/offers/halfling-height-requirement ● Pixie dust: http://www.disneyeveryday.com/bottle-of-tinker-bells-pixie-dust-neck lace/ ● Iceberg of Ignorance: https://corporate-rebels.com/iceberg-of-ignorance/