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Taking AppSec to 11
AppSec Pipelines, DevOps,
and Making Things Better.
AppSec California 2016
Matt Tesauro, Infinitiv
Assembly Lines
The Phoenix
Project
3 Ways of DevOps
Strategies for
Improving Operations
#1 - Workflow
Look at your purpose
and those processes
which aid it
Timeline
Business Operations Customer
Flow [rate] – the speed work goes through the process
Development
#1 Workflow
First of the three ways
- Each Step Repeatable
- Never Pass on Defects
- Local optimizations with a global view
AppSec Pipelines
Figuring out your workflow
AppSec Pipelines
Key Features of
AppSec Pipelines
◇ Designed for iterative improvement
◇ Provides a reusable path for AppSec activities to
follow
◇ Provides a consistent process for both the team and
our constituency
◇ One way flow with well-defined states
◇ Relies heavily on automation
◇ Grow in functionality organically over time
◇ Gracefully interconnects with the development
process
Pearson AppSec Pipeline
Integrating into the DevOps Pipeline
DevOps Pipeline AppSec Pipeline
“
Spending time
optimizing anything
other than the critical
resource is an illusion.
W. Edwards Deming
Key Goals of
AppSec Pipelines
◇ Optimize the critical resource - AppSec personnel
■ Automate all the things that don’t require a
human brain
■ Drive up consistency
■ Increase tracking of work status
■ Increase flow through the system
■ Increase visibility and metrics
■ Reduce any dev team friction with application
security
Pipeline - Intake
◇ “First Impression”
◇ Major categories of Intake
■ Existing App
■ New App
■ Previously tested App
■ App to re-test findings
◇ Key Concepts
■ Ask for data about Apps only once
■ Have data reviewed when an App
returns
■ Adapt data collected based on broad
categories of Apps
Pipeline - Testing
◇ Inbound request triage
◇ Ala Carte App Sec
■ Dynamic Testing
■ Static Testing
■ Re-Testing mitigated findings
■ Mix and match based on risk
◇ Key Concepts
■ Activities can be run in
parallel
■ Automation on setup,
configuration, data export
◇ People focus on customization
rather than setup
Pipeline - Testing
◇ Results from your CI/CD could flow into Threadfix from
build Pipeline
◇ Gauntlt runs results could also flow into the AppSec
Pipeline
◇ Choose the tools that make sense for you organization
Pipeline - Deliver
◇ Source of truth for all AppSec
activities
◇ ThreadFix is used to
■ Dedup / Consolidate findings
■ Normalize scanner data
■ Generate Metrics
■ Push issues to bug trackers
◇ Report and metrics automation
■ REST + tfclient
◇ Source of many touch points with
external teams
◇ Allow us to have visibility into WIP
◇ Better understand/track/optimize flow of
engagements
◇ Average static test takes ...
◇ Great increase in consistency
◇ Easier re-allocation of engagements between staff
◇ Each step has a well defined interface
◇ Knowing who has what allows for more informed
“cost of switching” conversations
◇ Flexible enough for a range of skills and
app maturity
Why we like AppSec
Pipelines
~5x increase
2014
44 assessments
2015
~200 assessments
Changes from 2014 to 2015:
- Created the AppSec Pipeline - initial launch in March 2015
- AppSec team numbers dropped - lost a couple of key people approx 3.5 FTEs
- Two of the AppSec team members went meta for most of 2015
Bag of Holding
aka BoH
github.com/PearsonEducation/bag-of-holding
◇ Manages the Application Security Program
◇ Application Repository
◇ Engagement Tracking
◇ Report Repository
◇ Comments on any application, engagement or activity
◇ Data Classification and PII data
◇ Time taken on secure software activities
◇ Historical knowledge of past assessments
◇ Credential repository
◇ Environment details
What does BoH do?
Scheduling of Secure
Software Activities
Application Repository
Application Security Profile
Defect Dojo
◇ DefectDojo is a tool created by the Security
Engineering team at Rackspace to track testing
efforts.
◇ Streamlines the testing process by offering features
such as templating, report generation, metrics, and
baseline self-service tools.
◇ Though it was designed with security folks in mind,
there is nothing keeping QA/QE testers, or any other
testers for that matter, from using it productively.
◇ https://github.com/rackerlabs/django-DefectDojo
Open yourself to upstream
and downstream information
#2 - Improve Feedback
AppSec ChatOps
aka Will
Your command line where you have your
conversations.
AppSec Help
AppSec Advice
Threadfix Integration
And more:
• Create an Application
• Get Summary Metrics for
AppSec Program
BOH/Threadfix/Static
Integration
Setup recurring static analysis in about 1 minute!
Create a culture of innovation and
experimentation
#3 - Continual
Experimentation &
Learning
“I fear not the man
who has practiced
ten thousand kicks
once,
but I fear the man
who has practiced
one kick ten thousand
times.”
Dev & AppSec Tool Integration
OWASP ZAP
Proxy
BuildManageCode Store
RAPTOR
Deploy
OWASP ZAP
Proxy
*Not a comprehensive list. The OWASP DevOps AppSec Pipeline will have a complete listing.
Demo Time
A quick bit of show and tell...
Key Take Aways
◇ Automate, automate, automate
■ Look for “paper cuts” and fix those first
◇ Finding workflow – your AppSec Pipeline
■ Figure this out and standardize / optimize
◇ Create systems which can grow organically
■ App is never done, it’s just created to easily be
added to over time
■ e.g. Finding blocks become templates for next
report
◇ Learn to talk “dev”
Thanks!
Matt Tesauro
@matt_tesauro
matt.tesauro@infinitiv.io
matt.tesauro@owasp.org
/in/matttesauro
github.com/mtesauro
Resources
Exercises left to the student
Orchestration
◇ Integrate Security Tools and Workflow
Example:
◇ Generic API for dynamic scanning
■ URL
■ Credentials
■ Profile
■ Call any Dynamic Scanner:
○ OWASP ZAP
○ BurpSuite
○ AppScan
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
Tiaga
◇ Project Management Software
■ Focused on usability and speed
■ Kanban / Scrum
■ Backlog
■ Tasks
■ Sprints
■ Issues
■ Wiki
◇ Open Source – Python / Django app
■ Entire functionality is driven by a REST API !!
■ https://taiga.io/
Defect Dojo
◇ DefectDojo is a tool created by the Security
Engineering team at Rackspace to track testing
efforts.
◇ Streamlines the testing process by offering features
such as templating, report generation, metrics, and
baseline self-service tools.
◇ Though it was designed with security folks in mind,
there is nothing keeping QA/QE testers, or any other
testers for that matter, from using it productively.
◇ https://github.com/rackerlabs/django-DefectDojo
Experimentation
Kick things up a notch
Findings directly to
bug trackers
◇ PDFs are great, bugs are better
◇ Security issues are now part of the normal work flow
◇ ThreadFix is nice for pumping issues into defect
trackers - http://code.google.com/p/threadfix/
For the reticent: nag,
nag, nag
◇ Attach a SLA to each severity level for findings
◇ Walk up the Org chart as things get older
◇ Bonus points for dashboards and defect tracker APIs
◇ Get management sold first
Agent – one mole to
rule them all
◇ Add an agent to the standard deploy
◇ Add a dashboard to visualize state of infrastructure
◇ Roll your own or find a vendor
Mozilla MIG
Turn Vuln Scanning on
its Head
◇ Add value for your Ops teams
◇ Roll your own or find a vendor
◇ Reverse the scan then report standard
Related Presentations
AppSec EU 2015 – Ops Track Keynote
http://www.slideshare.net/mtesauro/mtesauro-keynote-appseceu
https://www.youtube.com/watch?v=tDnyFitE0y4
AppSec EU 2015 – Building an AppSec Pipeline
http://www.slideshare.net/weaveraaaron/building-an-appsec-
pipeline-keeping-your-program-and-your-life-sane
https://www.youtube.com/watch?v=1CDSOSl4DQU
Books to Read
#1 Workflow
Each Step Repeatable
◇ Remove all haphazard and ad hoc work from the
process
◇ Scripting languages are your friends
◇ Config Mgmt – Puppet, Chef, Salt, Ansible, CFEngine
◇ Make sure what you do can be done on 1 server or
10,000 servers
#1 Workflow
Never Pass on Defects
◇ Test early and often
◇ Increase the rigor of testing as you work left to right
◇ When a failure occurs end that flow and start a new
one after corrections
◇ The further right you are, the more expensive failure is
so concentrate your early work on left side (intake)
◇ In AppSec, defects are false positives
#1 Workflow
Local optimizations with a global view
◇ Ensure no single-step optimizations degrade the
overall performance of the workflow
◇ Find the bottleneck in your workflow and start there
■ Upstream changes will just back things up
■ Downstream changes won't manifest since input
is limited
◇ Each new optimization creates a new bottleneck
■ Iterate on this!
“
Spending time
optimizing anything
other than the critical
resource is an illusion.
W. Edwards Deming
Japan's post-war miracle
Henry Ford in a field:
http://henryfordgiantdifferenceaward.weebly.com/works-cited.html
Assembly Lines:
http://www.pictofcar.website/henry-ford-assembly-line-diagram/
http://www.fasttrackteaching.com/burns/Unit_3_Industry/U3_Ford.html
http://en.wikipedia.org/wiki/Assembly_line
http://actionspeaksradio.org/tag/henry-ford/
http://blogs.internetautoguide.com/6582595/manufacturing/henry-ford-didnt-invent-the-assembly-line-
ransom-e-olds-did/index.html
W. Edward Deming
http://www.motortrend.com/features/consumer/1005_30_who_count/photo_04.html
Japan's Post War Miracle
http://www2.fultonschools.org/teacher/robertsw1/thursday.nov1.htm
http://dylewski.com.pl/menu-boczne/iluzja-pieniadza/usa-vs-japonia/
http://en.wikipedia.org/wiki/Japanese_post-war_economic_miracle
Image References
Thomas Edison:
http://www.allposters.com/-sp/Thomas-Edison-Posters_i1859026_.htm
Food line:
http://www.slideshare.net/weaveraaaron/building-an-appsec-pipeline-keeping-your-program-and-your-life-
sane
Phoenix Project Book Cover:
https://puppetlabs.com/blog/why-we-need-devops-now
Goes to 11:
https://arturogalletti.files.wordpress.com/2010/12/spinaltap.jpg
Image References
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Taking AppSec to 11: AppSec Pipeline, DevOps and Making Things Better

  • 1. Taking AppSec to 11 AppSec Pipelines, DevOps, and Making Things Better. AppSec California 2016 Matt Tesauro, Infinitiv
  • 2.
  • 4.
  • 5. The Phoenix Project 3 Ways of DevOps Strategies for Improving Operations
  • 6. #1 - Workflow Look at your purpose and those processes which aid it
  • 7. Timeline Business Operations Customer Flow [rate] – the speed work goes through the process Development
  • 8. #1 Workflow First of the three ways - Each Step Repeatable - Never Pass on Defects - Local optimizations with a global view
  • 10.
  • 12.
  • 13. Key Features of AppSec Pipelines ◇ Designed for iterative improvement ◇ Provides a reusable path for AppSec activities to follow ◇ Provides a consistent process for both the team and our constituency ◇ One way flow with well-defined states ◇ Relies heavily on automation ◇ Grow in functionality organically over time ◇ Gracefully interconnects with the development process
  • 15. Integrating into the DevOps Pipeline DevOps Pipeline AppSec Pipeline
  • 16. “ Spending time optimizing anything other than the critical resource is an illusion. W. Edwards Deming
  • 17. Key Goals of AppSec Pipelines ◇ Optimize the critical resource - AppSec personnel ■ Automate all the things that don’t require a human brain ■ Drive up consistency ■ Increase tracking of work status ■ Increase flow through the system ■ Increase visibility and metrics ■ Reduce any dev team friction with application security
  • 18. Pipeline - Intake ◇ “First Impression” ◇ Major categories of Intake ■ Existing App ■ New App ■ Previously tested App ■ App to re-test findings ◇ Key Concepts ■ Ask for data about Apps only once ■ Have data reviewed when an App returns ■ Adapt data collected based on broad categories of Apps
  • 19. Pipeline - Testing ◇ Inbound request triage ◇ Ala Carte App Sec ■ Dynamic Testing ■ Static Testing ■ Re-Testing mitigated findings ■ Mix and match based on risk ◇ Key Concepts ■ Activities can be run in parallel ■ Automation on setup, configuration, data export ◇ People focus on customization rather than setup
  • 20. Pipeline - Testing ◇ Results from your CI/CD could flow into Threadfix from build Pipeline ◇ Gauntlt runs results could also flow into the AppSec Pipeline ◇ Choose the tools that make sense for you organization
  • 21. Pipeline - Deliver ◇ Source of truth for all AppSec activities ◇ ThreadFix is used to ■ Dedup / Consolidate findings ■ Normalize scanner data ■ Generate Metrics ■ Push issues to bug trackers ◇ Report and metrics automation ■ REST + tfclient ◇ Source of many touch points with external teams
  • 22. ◇ Allow us to have visibility into WIP ◇ Better understand/track/optimize flow of engagements ◇ Average static test takes ... ◇ Great increase in consistency ◇ Easier re-allocation of engagements between staff ◇ Each step has a well defined interface ◇ Knowing who has what allows for more informed “cost of switching” conversations ◇ Flexible enough for a range of skills and app maturity Why we like AppSec Pipelines
  • 23. ~5x increase 2014 44 assessments 2015 ~200 assessments Changes from 2014 to 2015: - Created the AppSec Pipeline - initial launch in March 2015 - AppSec team numbers dropped - lost a couple of key people approx 3.5 FTEs - Two of the AppSec team members went meta for most of 2015
  • 24. Bag of Holding aka BoH github.com/PearsonEducation/bag-of-holding
  • 25. ◇ Manages the Application Security Program ◇ Application Repository ◇ Engagement Tracking ◇ Report Repository ◇ Comments on any application, engagement or activity ◇ Data Classification and PII data ◇ Time taken on secure software activities ◇ Historical knowledge of past assessments ◇ Credential repository ◇ Environment details What does BoH do?
  • 29. Defect Dojo ◇ DefectDojo is a tool created by the Security Engineering team at Rackspace to track testing efforts. ◇ Streamlines the testing process by offering features such as templating, report generation, metrics, and baseline self-service tools. ◇ Though it was designed with security folks in mind, there is nothing keeping QA/QE testers, or any other testers for that matter, from using it productively. ◇ https://github.com/rackerlabs/django-DefectDojo
  • 30.
  • 31. Open yourself to upstream and downstream information #2 - Improve Feedback
  • 32.
  • 34. Your command line where you have your conversations.
  • 37. Threadfix Integration And more: • Create an Application • Get Summary Metrics for AppSec Program
  • 39. Create a culture of innovation and experimentation #3 - Continual Experimentation & Learning
  • 40.
  • 41. “I fear not the man who has practiced ten thousand kicks once, but I fear the man who has practiced one kick ten thousand times.”
  • 42.
  • 43. Dev & AppSec Tool Integration OWASP ZAP Proxy BuildManageCode Store RAPTOR Deploy OWASP ZAP Proxy *Not a comprehensive list. The OWASP DevOps AppSec Pipeline will have a complete listing.
  • 44. Demo Time A quick bit of show and tell...
  • 45. Key Take Aways ◇ Automate, automate, automate ■ Look for “paper cuts” and fix those first ◇ Finding workflow – your AppSec Pipeline ■ Figure this out and standardize / optimize ◇ Create systems which can grow organically ■ App is never done, it’s just created to easily be added to over time ■ e.g. Finding blocks become templates for next report ◇ Learn to talk “dev”
  • 48. Orchestration ◇ Integrate Security Tools and Workflow Example: ◇ Generic API for dynamic scanning ■ URL ■ Credentials ■ Profile ■ Call any Dynamic Scanner: ○ OWASP ZAP ○ BurpSuite ○ AppScan
  • 49. 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
  • 50. Tiaga ◇ Project Management Software ■ Focused on usability and speed ■ Kanban / Scrum ■ Backlog ■ Tasks ■ Sprints ■ Issues ■ Wiki ◇ Open Source – Python / Django app ■ Entire functionality is driven by a REST API !! ■ https://taiga.io/
  • 51.
  • 52.
  • 53. Defect Dojo ◇ DefectDojo is a tool created by the Security Engineering team at Rackspace to track testing efforts. ◇ Streamlines the testing process by offering features such as templating, report generation, metrics, and baseline self-service tools. ◇ Though it was designed with security folks in mind, there is nothing keeping QA/QE testers, or any other testers for that matter, from using it productively. ◇ https://github.com/rackerlabs/django-DefectDojo
  • 54.
  • 56. Findings directly to bug trackers ◇ PDFs are great, bugs are better ◇ Security issues are now part of the normal work flow ◇ ThreadFix is nice for pumping issues into defect trackers - http://code.google.com/p/threadfix/
  • 57. For the reticent: nag, nag, nag ◇ Attach a SLA to each severity level for findings ◇ Walk up the Org chart as things get older ◇ Bonus points for dashboards and defect tracker APIs ◇ Get management sold first
  • 58. Agent – one mole to rule them all ◇ Add an agent to the standard deploy ◇ Add a dashboard to visualize state of infrastructure ◇ Roll your own or find a vendor Mozilla MIG
  • 59. Turn Vuln Scanning on its Head ◇ Add value for your Ops teams ◇ Roll your own or find a vendor ◇ Reverse the scan then report standard
  • 60. Related Presentations AppSec EU 2015 – Ops Track Keynote http://www.slideshare.net/mtesauro/mtesauro-keynote-appseceu https://www.youtube.com/watch?v=tDnyFitE0y4 AppSec EU 2015 – Building an AppSec Pipeline http://www.slideshare.net/weaveraaaron/building-an-appsec- pipeline-keeping-your-program-and-your-life-sane https://www.youtube.com/watch?v=1CDSOSl4DQU
  • 62. #1 Workflow Each Step Repeatable ◇ Remove all haphazard and ad hoc work from the process ◇ Scripting languages are your friends ◇ Config Mgmt – Puppet, Chef, Salt, Ansible, CFEngine ◇ Make sure what you do can be done on 1 server or 10,000 servers
  • 63. #1 Workflow Never Pass on Defects ◇ Test early and often ◇ Increase the rigor of testing as you work left to right ◇ When a failure occurs end that flow and start a new one after corrections ◇ The further right you are, the more expensive failure is so concentrate your early work on left side (intake) ◇ In AppSec, defects are false positives
  • 64. #1 Workflow Local optimizations with a global view ◇ Ensure no single-step optimizations degrade the overall performance of the workflow ◇ Find the bottleneck in your workflow and start there ■ Upstream changes will just back things up ■ Downstream changes won't manifest since input is limited ◇ Each new optimization creates a new bottleneck ■ Iterate on this!
  • 65. “ Spending time optimizing anything other than the critical resource is an illusion.
  • 68. Henry Ford in a field: http://henryfordgiantdifferenceaward.weebly.com/works-cited.html Assembly Lines: http://www.pictofcar.website/henry-ford-assembly-line-diagram/ http://www.fasttrackteaching.com/burns/Unit_3_Industry/U3_Ford.html http://en.wikipedia.org/wiki/Assembly_line http://actionspeaksradio.org/tag/henry-ford/ http://blogs.internetautoguide.com/6582595/manufacturing/henry-ford-didnt-invent-the-assembly-line- ransom-e-olds-did/index.html W. Edward Deming http://www.motortrend.com/features/consumer/1005_30_who_count/photo_04.html Japan's Post War Miracle http://www2.fultonschools.org/teacher/robertsw1/thursday.nov1.htm http://dylewski.com.pl/menu-boczne/iluzja-pieniadza/usa-vs-japonia/ http://en.wikipedia.org/wiki/Japanese_post-war_economic_miracle Image References
  • 69. Thomas Edison: http://www.allposters.com/-sp/Thomas-Edison-Posters_i1859026_.htm Food line: http://www.slideshare.net/weaveraaaron/building-an-appsec-pipeline-keeping-your-program-and-your-life- sane Phoenix Project Book Cover: https://puppetlabs.com/blog/why-we-need-devops-now Goes to 11: https://arturogalletti.files.wordpress.com/2010/12/spinaltap.jpg Image References
  • 70. What’s this? This is a free presentation template for Google Slides designed by SlidesCarnival. We believe that good design serves to better communicate ideas, so we create free quality presentation templates for you to focus on the content. Enjoy them at will and share with us your results at: twitter.com/SlidesCarnival facebook.com/slidescarnival About this template How can I use it? Open this document in Google Slides (if you are at slidescarnival. com use the button below this presentation) You have to be signed in to your Google account ◇ Edit in Google Slides Go to the File menu and select Make a copy. You will get a copy of this document on your Google Drive and will be able to edit, add or delete slides. ◇ Edit in Microsoft PowerPoint® Go to the File menu and select Download as Microsoft PowerPoint. You will get a .pptx file that you can edit in PowerPoint. Remember to download and install the fonts used in this presentation (you’ll find the links to the font files needed in the Presentation design slide) This template is free to use under Creative Commons Attribution license. If you use the graphic assets (photos, icons and typographies) provided with this presentation you must keep the Credits slide.