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Making Security as Agile as Dev:
Adding DevOps and TDD to your security program
Matt Tesauro
OWASP San Antonio
March 2015
Who am I?
4 months with Pearson
Application Security Lead Engineer
Prior to Pearson
● Rackspace - Lead Engineer, Product Security
● AppSec consulting
o VP Services, Praetorian
o Consultant Trustwave’s Spiderlabs
● TEA - Senior Security Engineer
● DIR - Penetration Tester
● Texas A&M University
o Systems Analyst, Sys Admin, Developer, DBA
o Lecturer in MIS department
● Viatel -
Internet App Developer
Who am I?
Other professional experience
● OWASP Live CD / OWASP WTE
o Project lead 2008 to present
o Over 300K downloads
o http://appseclive.org
● OWASP Foundation Board of Directors
o International charity focused on improving the security of
software
● Multiple speaking engagements internationally
at AppSec, DHS, ISC2, … conferences
● Application Security Training internationally
Making Security Agile
CI, CD, CD, TDD and API
CI == Continuous Integration
CD == Continuous Deployment
CD == Continuous Delivery
TDD == Test Driven Development
API == Application Programming Interface
• Cycle time for software is getting
shorter
• Continuous delivery is a goal
• Scanning windows are not viable
• First mover / first to market
advantage
The Problem
The Problem – or at least more problems
• Traditional software development left little time to test
• DevOps, Agile and Continuous Delivery squeeze those windows
even more
• New languages and programming methods aren’t making
this better
• Growth of interpreted languages with loose typing
hurts static analysis efforts
• Few automated tools to test APIs especially
RESTful APIs
• Little time for any testing, manual testing is doomed
• Automated software
testing
• Automated operational
infrastructure
• Automated security
testing
THE SOLUTION
Think like a developer
Sprints break software into little pieces…
• Break your testing into little pieces
• Use your threat model to know the crucial bits to test
Long and short running tests
• Testing time drives testing frequency
• Code for tests needs to be optimized
Smoke test versus full regression test
• Smoke test early and often
• Full regression tests on regular intervals
Maximize what you’ve got
Make the most of your frameworks
•Embrace, understand and fill gaps where necessary
Make the best use of your time…
• Make tests easily repeatable
• Make tests easy to understand
• Make tests abstract and combine-able
• Ala carte tests for mixing and matching
• Think about the Unix pipe | and its power
Under the constraints of DevOps, Continuous Deployment
Your testing has to be nimble
Dare I say…Agile
In TDD, you know your code works
when the tests pass
In TD(S), you know your app has met
the baseline when the tests pass
Test Driven Development Security
A time to morn...
• Securing Infrastructure
• Securing Apps and APIs
• Securing Code
Automate yourself into an agile state by...
Securing Infrastructure
Automating Infrastructure
• Declarative configuration language
• Plain-text configuration in source control
• Fully programmatic, no manual interactions
Most of these work like...
1. Ad Hoc
2. Local runs
3. Hosted/SaaS
4. Private Hosted Node
Node
Node
Node
Node
Node
Node
Node
Node
Node
Node
Node
Node
Node
Node
Sys
Admin
The Mother Ship
Cookbooks, Stacks, Playbooks, ...
• Most have methods to
bundle / share
automation routines
• You will have to write
your own / customize
• Good place to spend
security cycles
-Merge patches upstream for
extra points.
Grouping & Tagging
• Tagging your
servers applies
the required set of
automation
• A base set of for
all servers
• Each server can
have multiple tags
• Map tags to
security
requirements
Node
Node
Node
Node
DB
Node
Node
Node
Node
Cache
Node
Node
Node
Node
Web
Apache
Monitoring
MySql
Memcache
Works for Clouds Too!
Inspector – you need one
• For each group and/or tag
• Review the recipe, do a PR
• Hook provisioning for post deploy review
• Focus on checking for code compliance
-Not perfection, bare minimums
• Can include multiple facets
-Security, Scalability, Compliance
• Vuln scanners – manual or auto
• Jenkins Job + Lynis (open source)
Agent – one mole to rule them all
• Add an agent to the standard deploy
• Read-only helps sell to SysAdmin
• Looks at the state of the system
• Reports the state to the “mothership”
• Add a dashboard to visualize state of infrastructure
• Change policy, servers go red
• Watch the board go green as patches roll-out
• Roll your own or find a vendor
Mozilla MIG
Turn Vuln scanning on its head
• Add value for your ops teams
• Subscribe and parse vuln emails for key software
• Get this info during threat models or config mgmt
• Provide an early warning and remove panic from
software updates
• Roll your own or find a vendor
• Gmail + filters can work surprisingly well
• Secunia VIM covers 40K+ products
• Reverse the scan then report standard
Securing Apps and APIs
Findings directly to bug trackers
• PDFs are great, bugs are better
• Work with developer teams to submit bugs
• Security category needs to exist
• Bonus points if the bug tracker has an API
• Security issues are now part of the normal work flow
• Beware of death by backlog
• Occasional security sprints
• Learn how the team treats issues
• ThreadFix is nice for metrics and pumping issues into
issue trackers - http://code.google.com/p/threadfix/
For the reticent: nag, nag, nag
• Attach a SLA to each severity level for findings
• Remediation plan vs Fixed
• “Age” all findings against these SLAs
• Politely warn when SLA dates are close
• Walk up the Org chart as things
get older
• Bonus points for dashboards and
bug tracker APIs
• Get management sold first
Reports = Findings + Automation
• Consider markup for findings
• Markdown, Wiki Text, asciidoc
• Pandoc to convert to whatever
• HTML, PDF, .doc, .odt, ...
• Keep testers writing the least possible
• Template and re-use boiler plate items
• New finding == new template for next time
• Web app to keep things consistent
• Push or Pull from Threadfix via API
Leverage existing consistencies
• Requires consistent (generally automated) input
• Find these and write some scripts
• Automate the drudgery
• Examples:
• Automate finding/bug submission
• Automate report PDF generation
• API documentation to basic testing harness
• Sec tool output – combine and convert
Securing Code
Start with the developers
• Finding details have to be detailed enough to:
• Reproduce the issue after 6 months
• Allow QA/QE to test the issue
• Allow developers to find/fix the issue
• Consider quick and dirty scripts to reproduce issue
• Script to abuse an API
• Web page of reflective XSS findings
• Gauntlt - http://gauntlt.org/
• Once findings start flowing, look for training requests
Cherry pick what you look at
• Threat Models are your friends
• Focus on weak, unclear or suspicious areas
• Focus on connections with external systems
• Focus on format translations (XML to JSON)
• When code changes in those areas,
• Red flag it for review
• Change +2 to +3 to before accepting pull request
• Use search features in source code management
• Start a list of problematic methods, calls, etc
No False Positive, period.
• If you can automate code review, you still must triage
• 1 false positive == 100 valid bugs
• If results aren't actionable, fail
• Stick to diff analysis
• Threat Modeling + “Scary Parts” + Code diffs
== Quick triage of code changes
• Automate where you can, iterate until you're happy
• Need to build cred points with the dev teams
Quiet is better then wrong
• Hire or befriend developers
• Need to speak their language, not security's
• Suggest requirements not implementation
• Mitigation suggestions either generic or in the
language the app is written in
• Remember: Fast deploys also means fast fixes
• Trying to shrink any vuln window not eliminate
• Be prepared to retest / verify fix quickly
What is happening
at Pearson?
Say hello to my little friend...
The AppSec Pipeline
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
• Has the ability to grow in functionality organically over
time
• Gracefully interconnects with the development process
Spending time optimizing anything
other than the critical resource
is an illusion.
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 impedance 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 – the Middle
• 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
• Focus on customization rather than
setup
Pipeline – the End
• 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
Why we like AppSec Pipelines
• 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
Key Take Aways...
• Automate, automate, automate
• Look for “paper cuts” and fix those first
• Finding workflow
• Figure this out and standardize / optimize
• Create systems which can grow organically
• App is never done, its just created to easily be
added to over time
• Finding blocks become templates for next time
• Learn to talk “dev”
The AppSec Pipeline
Change is here and more is coming...
"Whosoever desires constant
success must change his conduct
with the times."
— Niccolo Machiavelli
Questions?
Thank You
5 Stages of Grief
This agile thing is a fad...
Waterfall is the only way to produce
quality software...
5 Stages of Grief
There's no way I can test in that time
frame...
If I see another freaking sticky note...
5 Stages of Grief
Well, I think I can test some of it in
two days...
I guess I can test it after its deployed
to prod...
5 Stages of Grief
After that launch, I updated my
LinkedIn profile...
Game over man, GAME OVER...
(Thanks Aliens)
5 Stages of Grief
So when can you add a story to work
on that auth regression...
After reviewing your deployment
recipe, we filed a pull request to fix...

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Making security-agile matt-tesauro

  • 1. Making Security as Agile as Dev: Adding DevOps and TDD to your security program Matt Tesauro OWASP San Antonio March 2015
  • 2. Who am I? 4 months with Pearson Application Security Lead Engineer Prior to Pearson ● Rackspace - Lead Engineer, Product Security ● AppSec consulting o VP Services, Praetorian o Consultant Trustwave’s Spiderlabs ● TEA - Senior Security Engineer ● DIR - Penetration Tester ● Texas A&M University o Systems Analyst, Sys Admin, Developer, DBA o Lecturer in MIS department ● Viatel - Internet App Developer
  • 3. Who am I? Other professional experience ● OWASP Live CD / OWASP WTE o Project lead 2008 to present o Over 300K downloads o http://appseclive.org ● OWASP Foundation Board of Directors o International charity focused on improving the security of software ● Multiple speaking engagements internationally at AppSec, DHS, ISC2, … conferences ● Application Security Training internationally
  • 5. CI, CD, CD, TDD and API CI == Continuous Integration CD == Continuous Deployment CD == Continuous Delivery TDD == Test Driven Development API == Application Programming Interface
  • 6. • Cycle time for software is getting shorter • Continuous delivery is a goal • Scanning windows are not viable • First mover / first to market advantage The Problem
  • 7. The Problem – or at least more problems • Traditional software development left little time to test • DevOps, Agile and Continuous Delivery squeeze those windows even more • New languages and programming methods aren’t making this better • Growth of interpreted languages with loose typing hurts static analysis efforts • Few automated tools to test APIs especially RESTful APIs • Little time for any testing, manual testing is doomed
  • 8. • Automated software testing • Automated operational infrastructure • Automated security testing THE SOLUTION
  • 9. Think like a developer Sprints break software into little pieces… • Break your testing into little pieces • Use your threat model to know the crucial bits to test Long and short running tests • Testing time drives testing frequency • Code for tests needs to be optimized Smoke test versus full regression test • Smoke test early and often • Full regression tests on regular intervals
  • 10. Maximize what you’ve got Make the most of your frameworks •Embrace, understand and fill gaps where necessary Make the best use of your time… • Make tests easily repeatable • Make tests easy to understand • Make tests abstract and combine-able • Ala carte tests for mixing and matching • Think about the Unix pipe | and its power
  • 11. Under the constraints of DevOps, Continuous Deployment Your testing has to be nimble Dare I say…Agile In TDD, you know your code works when the tests pass In TD(S), you know your app has met the baseline when the tests pass Test Driven Development Security
  • 12. A time to morn...
  • 13. • Securing Infrastructure • Securing Apps and APIs • Securing Code Automate yourself into an agile state by...
  • 15. Automating Infrastructure • Declarative configuration language • Plain-text configuration in source control • Fully programmatic, no manual interactions
  • 16. Most of these work like... 1. Ad Hoc 2. Local runs 3. Hosted/SaaS 4. Private Hosted Node Node Node Node Node Node Node Node Node Node Node Node Node Node Node Sys Admin The Mother Ship
  • 17. Cookbooks, Stacks, Playbooks, ... • Most have methods to bundle / share automation routines • You will have to write your own / customize • Good place to spend security cycles -Merge patches upstream for extra points.
  • 18. Grouping & Tagging • Tagging your servers applies the required set of automation • A base set of for all servers • Each server can have multiple tags • Map tags to security requirements Node Node Node Node DB Node Node Node Node Cache Node Node Node Node Web Apache Monitoring MySql Memcache Works for Clouds Too!
  • 19. Inspector – you need one • For each group and/or tag • Review the recipe, do a PR • Hook provisioning for post deploy review • Focus on checking for code compliance -Not perfection, bare minimums • Can include multiple facets -Security, Scalability, Compliance • Vuln scanners – manual or auto • Jenkins Job + Lynis (open source)
  • 20. Agent – one mole to rule them all • Add an agent to the standard deploy • Read-only helps sell to SysAdmin • Looks at the state of the system • Reports the state to the “mothership” • Add a dashboard to visualize state of infrastructure • Change policy, servers go red • Watch the board go green as patches roll-out • Roll your own or find a vendor Mozilla MIG
  • 21. Turn Vuln scanning on its head • Add value for your ops teams • Subscribe and parse vuln emails for key software • Get this info during threat models or config mgmt • Provide an early warning and remove panic from software updates • Roll your own or find a vendor • Gmail + filters can work surprisingly well • Secunia VIM covers 40K+ products • Reverse the scan then report standard
  • 23. Findings directly to bug trackers • PDFs are great, bugs are better • Work with developer teams to submit bugs • Security category needs to exist • Bonus points if the bug tracker has an API • Security issues are now part of the normal work flow • Beware of death by backlog • Occasional security sprints • Learn how the team treats issues • ThreadFix is nice for metrics and pumping issues into issue trackers - http://code.google.com/p/threadfix/
  • 24. For the reticent: nag, nag, nag • Attach a SLA to each severity level for findings • Remediation plan vs Fixed • “Age” all findings against these SLAs • Politely warn when SLA dates are close • Walk up the Org chart as things get older • Bonus points for dashboards and bug tracker APIs • Get management sold first
  • 25. Reports = Findings + Automation • Consider markup for findings • Markdown, Wiki Text, asciidoc • Pandoc to convert to whatever • HTML, PDF, .doc, .odt, ... • Keep testers writing the least possible • Template and re-use boiler plate items • New finding == new template for next time • Web app to keep things consistent • Push or Pull from Threadfix via API
  • 26. Leverage existing consistencies • Requires consistent (generally automated) input • Find these and write some scripts • Automate the drudgery • Examples: • Automate finding/bug submission • Automate report PDF generation • API documentation to basic testing harness • Sec tool output – combine and convert
  • 28. Start with the developers • Finding details have to be detailed enough to: • Reproduce the issue after 6 months • Allow QA/QE to test the issue • Allow developers to find/fix the issue • Consider quick and dirty scripts to reproduce issue • Script to abuse an API • Web page of reflective XSS findings • Gauntlt - http://gauntlt.org/ • Once findings start flowing, look for training requests
  • 29. Cherry pick what you look at • Threat Models are your friends • Focus on weak, unclear or suspicious areas • Focus on connections with external systems • Focus on format translations (XML to JSON) • When code changes in those areas, • Red flag it for review • Change +2 to +3 to before accepting pull request • Use search features in source code management • Start a list of problematic methods, calls, etc
  • 30. No False Positive, period. • If you can automate code review, you still must triage • 1 false positive == 100 valid bugs • If results aren't actionable, fail • Stick to diff analysis • Threat Modeling + “Scary Parts” + Code diffs == Quick triage of code changes • Automate where you can, iterate until you're happy • Need to build cred points with the dev teams
  • 31. Quiet is better then wrong • Hire or befriend developers • Need to speak their language, not security's • Suggest requirements not implementation • Mitigation suggestions either generic or in the language the app is written in • Remember: Fast deploys also means fast fixes • Trying to shrink any vuln window not eliminate • Be prepared to retest / verify fix quickly
  • 33. Say hello to my little friend...
  • 35. 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 • Has the ability to grow in functionality organically over time • Gracefully interconnects with the development process
  • 36. Spending time optimizing anything other than the critical resource is an illusion.
  • 37. 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 impedance with application security
  • 38. 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
  • 39. Pipeline – the Middle • 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 • Focus on customization rather than setup
  • 40. Pipeline – the End • 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
  • 41. Why we like AppSec Pipelines • 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
  • 43. • Automate, automate, automate • Look for “paper cuts” and fix those first • Finding workflow • Figure this out and standardize / optimize • Create systems which can grow organically • App is never done, its just created to easily be added to over time • Finding blocks become templates for next time • Learn to talk “dev”
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  • 48. Change is here and more is coming... "Whosoever desires constant success must change his conduct with the times." — Niccolo Machiavelli
  • 50. 5 Stages of Grief This agile thing is a fad... Waterfall is the only way to produce quality software...
  • 51. 5 Stages of Grief There's no way I can test in that time frame... If I see another freaking sticky note...
  • 52. 5 Stages of Grief Well, I think I can test some of it in two days... I guess I can test it after its deployed to prod...
  • 53. 5 Stages of Grief After that launch, I updated my LinkedIn profile... Game over man, GAME OVER... (Thanks Aliens)
  • 54. 5 Stages of Grief So when can you add a story to work on that auth regression... After reviewing your deployment recipe, we filed a pull request to fix...