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LinkedIn.com/in/LarryMaccherone
DevSecOps is not just
DevOps lipstick on a
traditional security pig
Larry Maccherone
LinkedIn.com/in/LarryMaccherone
DevSecOpsWave
JustMarketing?
LinkedIn.com/in/LarryMaccherone
Larry Maccherone
Larry_Maccherone@Comcast.com
Larry Maccherone
LinkedIn.com/in/LarryMaccherone
DevOps is fertile ground for the concepts
driving the DHS-sponsored Build-Security-In portal
that Noopur Davis, Gary McGraw, and I launched a decade ago
DevOps = opportunity for security
As DevOps exponentially speeds
up the pace of development
Bolt-on security by security
specialists wonā€™t scale
ā€¦ so security MUST be a primary
concern of the development team
LinkedIn.com/in/LarryMaccherone
What is DevOps?
LinkedIn.com/in/LarryMaccherone
What is DevOps?
ā€¢ A new role?
ā€¢ Partnership/communication/empathy between Dev and Ops?
ā€¢ CI/CD tools?
ā€¢ Automation?
ā€¢ Self-service?
ā€¢ Techniques like feature flags or traffic shaping?
ā€¢ ā€œMove fast and break thingsā€?
ā€¢ Culture change (systems thinking, continuous improvement, etc.)?
DevOps isā€¦
empowered engineering teams
taking ownership
of how their product
performs in production
LinkedIn.com/in/LarryMaccherone
DevOps ļƒ  different decisions
LinkedIn.com/in/LarryMaccherone
ā€œI donā€™t always test
but when I do, itā€™s
in productionā€
Mature DevOps practices
1. Develop in trunk
ā€¢ No long-lived branches
ā€¢ Short branches for code review, build-
checking, time-intensive test suites,
security scanning, etc.
ā€¢ Dead-end release branches OK
2. Partial/unvalidated features
behind toggles/flags and/or
traffic shaping
3. Automated validation ļƒ 
automated push to prod
LinkedIn.com/in/LarryMaccherone
Feature toggles & traffic shaping
ā€¢ Run-time switchable
ā€¢ Database backed
ā€¢ Also for safe-to-fail feature experiments
ā€¢ Build/deploy time
ā€¢ Common for micro-services & APIs
ā€¢ Traffic shaping
ā€¢ Rules engine + database backed
XRE Guideā€™s
Application Discovery Service (ADS)
XRE Guideā€™s
Redirector Traffic Shaping Router
LinkedIn.com/in/LarryMaccherone
What is Dev[Sec]Ops?
LinkedIn.com/in/LarryMaccherone
Security
LinkedIn.com/in/LarryMaccherone
Dev[Sec]Ops isā€¦
empowered engineering teams
taking ownership
of how their product
performs in production
[including security]
LinkedIn.com/in/LarryMaccherone
Dev[Sec]Ops Results
ā€¢ Dramatically faster time to market ļƒ 
happier customers ļƒ  more revenue
ā€¢ 5x lower rate of failures caused by changes1
ā€¢ 96x faster recovery from downtime failures1
Itā€™s scary to QA and Security, but ā€œmoving fast and breaking
thingsā€ leads to dramatically lower rates of customer
experienced defects and vulnerabilities
1Puppetā€™s 2017 State of DevOps Report
Build security in
more than bolt it on
Rely on empowered engineering teams
more than security specialists
Implement features securely
more than security features
Rely on continuous learning
more than end-of-phase gates
Build on culture change
more than policy enforcement
DevSecOpsManifesto
We, the Security Teamā€¦
Recognize that Engineering Teamsā€¦
ā€¢ Want to do the right thing
ā€¢ Are closer to the business context and will
make smart trade-off decisions between
security and other risks
ā€¢ Want information and assistance so they
can improve our security posture
Pledge toā€¦
ā€¢ Lower the cost/effort side
of any investment in
developer security tools or
practices
ā€¢ Assist 2x as much with
preventative initiatives as
we beg for your assistance
reacting to security
incidents
Understand thatā€¦
ā€¢ We are no longer gate keepers but rather tool-smiths and advisors
Credibility + Reliability + Empathy
Trust = ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”
Apparent self-interest
https://www.devsecopsdays.com/articles/trust-algorithm-applied-to-devsecops
Manysupposed
DevSecOpstoolsare
justlipstickonapig
Think of security testing tools
as just another testing suite
like those for
unit, acceptance, etc.
Dev[Sec]Ops Tool Landscape
Static Analysis (aka SAST)
ā€¢ Looks at source code
ā€¢ Data/control flow analysis
ā€¢ Prone to false positives
ā€¢ Rapid feedback for developers
ā€¢ Code fix suggestions
Dynamic
ā€¢ Exercises app via UI/API
ā€¢ Senses vulnerability by response to input
ā€¢ Zero? false positives. Report is an exploit
ā€¢ High false negatives
ā€¢ Difficult to implement especially w/ auth
ā€¢ Sometimes hard to find code to remediate
Runtime Application
Security Protection
(RASP)
ā€¢ Often uses same engine
as IAST
ā€¢ Reports on ā€œbadā€
behavior
ā€¢ Can abort transaction or
kill process to protect
Fuzzing (black box)
ā€¢ Instruments system (to varying degrees)
ā€¢ Sends unexpected input at API
ā€¢ Looks at response and instrumentation output
ā€¢ Great for testing protocols like SIP
ā€¢ Good for REST APIs
ā€¢ Potentially long run times
ā€¢ Hard to find code to remediate
Software Composition
Analysis (SCA)
for code imported
ā€¢ Identifies dependency and
version
ā€¢ Checks CVE/NVD + ā€¦ for
reported vulnerabilities
ā€¢ Proposes version/patch to
remediate
ā€¢ Checks license vs policy
ā€¢ Runs fast
ā€¢ Easy to implement
ā€¢ Best bang for buck!
IAST
ā€¢ Runtime code analysis
ā€¢ Combine dynamic/static
ā€¢ Low false positives
ā€¢ Depends on test coverage
ā€¢ Immature but getting there
Criteria for DevSecOps tools
ā€¢ Integrated and runs fast in pipeline for current dev cycle:
ā€¢ Parallelized with other test suites, orā€¦
ā€¢ In-series, orā€¦
ā€¢ Incremental parallelized/in-series from asynchronous baseline, orā€¦
ā€¢ Asynchronous out of pipeline for baseline/feedback for next dev cycle
ā€¢ Notifications the way the team wants: Slack, email, report,
dashboard, etc.
ā€¢ Interrupt the pipeline the way the team wants: break the build,
turn the merge button red, etc.
ā€¢ Environment-specific (dev, staging, prod, etc.) ā€policyā€
DevSecOps Tool recommendations
ā€¢ SCA (aka dependency checkers, open source security scanners) are
the best bang for the buck/effort. START HERE
ā€¢ Next implement IAST or SAST (together, we created a category
grouping these two called Primary Code Analysis). FAVOR IAST
ā€¢ Embed in pipeline and treat like an additional test suite.
ā€¢ For greenfield turn on all checkers and interrupt pipeline unless
automated security tests come up clean.
ā€¢ For legacy, ā€œstop the bleedingā€ by interrupting pipeline for NEW
issues and slowly turn up the interrupt policy until all legacy issues
are resolved. Plan to address all critical/high issues within 120 days.
LinkedIn.com/in/LarryMaccherone
LinkedIn.com/in/LarryMaccherone
What will happen to
security specialists?
ā€¦ similar to what happened to QA
Engineers with the Agile movement
ā€¦ they will join a
development team
ā€¦ or they will become
tool-smiths and advisors
LinkedIn.com/in/LarryMaccherone
Whatā€™s
next?
ā€¢ Questions?
ā€¢ Read about the Trust Algorithm
https://www.devsecopsdays.com/articles/
trust-algorithm-applied-to-devsecops
ā€¢ Connect with me
LinkedIn.com/in/LarryMaccherone

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DevSecOps Is Not Just DevOps Lipstick On A traditional Security Pig

  • 1. LinkedIn.com/in/LarryMaccherone DevSecOps is not just DevOps lipstick on a traditional security pig Larry Maccherone LinkedIn.com/in/LarryMaccherone
  • 4. DevOps is fertile ground for the concepts driving the DHS-sponsored Build-Security-In portal that Noopur Davis, Gary McGraw, and I launched a decade ago DevOps = opportunity for security
  • 5. As DevOps exponentially speeds up the pace of development Bolt-on security by security specialists wonā€™t scale ā€¦ so security MUST be a primary concern of the development team
  • 7. LinkedIn.com/in/LarryMaccherone What is DevOps? ā€¢ A new role? ā€¢ Partnership/communication/empathy between Dev and Ops? ā€¢ CI/CD tools? ā€¢ Automation? ā€¢ Self-service? ā€¢ Techniques like feature flags or traffic shaping? ā€¢ ā€œMove fast and break thingsā€? ā€¢ Culture change (systems thinking, continuous improvement, etc.)?
  • 8. DevOps isā€¦ empowered engineering teams taking ownership of how their product performs in production
  • 10. LinkedIn.com/in/LarryMaccherone ā€œI donā€™t always test but when I do, itā€™s in productionā€ Mature DevOps practices 1. Develop in trunk ā€¢ No long-lived branches ā€¢ Short branches for code review, build- checking, time-intensive test suites, security scanning, etc. ā€¢ Dead-end release branches OK 2. Partial/unvalidated features behind toggles/flags and/or traffic shaping 3. Automated validation ļƒ  automated push to prod
  • 11. LinkedIn.com/in/LarryMaccherone Feature toggles & traffic shaping ā€¢ Run-time switchable ā€¢ Database backed ā€¢ Also for safe-to-fail feature experiments ā€¢ Build/deploy time ā€¢ Common for micro-services & APIs ā€¢ Traffic shaping ā€¢ Rules engine + database backed XRE Guideā€™s Application Discovery Service (ADS) XRE Guideā€™s Redirector Traffic Shaping Router
  • 14. LinkedIn.com/in/LarryMaccherone Dev[Sec]Ops isā€¦ empowered engineering teams taking ownership of how their product performs in production [including security]
  • 15. LinkedIn.com/in/LarryMaccherone Dev[Sec]Ops Results ā€¢ Dramatically faster time to market ļƒ  happier customers ļƒ  more revenue ā€¢ 5x lower rate of failures caused by changes1 ā€¢ 96x faster recovery from downtime failures1 Itā€™s scary to QA and Security, but ā€œmoving fast and breaking thingsā€ leads to dramatically lower rates of customer experienced defects and vulnerabilities 1Puppetā€™s 2017 State of DevOps Report
  • 16. Build security in more than bolt it on Rely on empowered engineering teams more than security specialists Implement features securely more than security features Rely on continuous learning more than end-of-phase gates Build on culture change more than policy enforcement DevSecOpsManifesto
  • 17. We, the Security Teamā€¦ Recognize that Engineering Teamsā€¦ ā€¢ Want to do the right thing ā€¢ Are closer to the business context and will make smart trade-off decisions between security and other risks ā€¢ Want information and assistance so they can improve our security posture Pledge toā€¦ ā€¢ Lower the cost/effort side of any investment in developer security tools or practices ā€¢ Assist 2x as much with preventative initiatives as we beg for your assistance reacting to security incidents Understand thatā€¦ ā€¢ We are no longer gate keepers but rather tool-smiths and advisors
  • 18. Credibility + Reliability + Empathy Trust = ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€”ā€” Apparent self-interest https://www.devsecopsdays.com/articles/trust-algorithm-applied-to-devsecops
  • 20. Think of security testing tools as just another testing suite like those for unit, acceptance, etc.
  • 21. Dev[Sec]Ops Tool Landscape Static Analysis (aka SAST) ā€¢ Looks at source code ā€¢ Data/control flow analysis ā€¢ Prone to false positives ā€¢ Rapid feedback for developers ā€¢ Code fix suggestions Dynamic ā€¢ Exercises app via UI/API ā€¢ Senses vulnerability by response to input ā€¢ Zero? false positives. Report is an exploit ā€¢ High false negatives ā€¢ Difficult to implement especially w/ auth ā€¢ Sometimes hard to find code to remediate Runtime Application Security Protection (RASP) ā€¢ Often uses same engine as IAST ā€¢ Reports on ā€œbadā€ behavior ā€¢ Can abort transaction or kill process to protect Fuzzing (black box) ā€¢ Instruments system (to varying degrees) ā€¢ Sends unexpected input at API ā€¢ Looks at response and instrumentation output ā€¢ Great for testing protocols like SIP ā€¢ Good for REST APIs ā€¢ Potentially long run times ā€¢ Hard to find code to remediate Software Composition Analysis (SCA) for code imported ā€¢ Identifies dependency and version ā€¢ Checks CVE/NVD + ā€¦ for reported vulnerabilities ā€¢ Proposes version/patch to remediate ā€¢ Checks license vs policy ā€¢ Runs fast ā€¢ Easy to implement ā€¢ Best bang for buck! IAST ā€¢ Runtime code analysis ā€¢ Combine dynamic/static ā€¢ Low false positives ā€¢ Depends on test coverage ā€¢ Immature but getting there
  • 22. Criteria for DevSecOps tools ā€¢ Integrated and runs fast in pipeline for current dev cycle: ā€¢ Parallelized with other test suites, orā€¦ ā€¢ In-series, orā€¦ ā€¢ Incremental parallelized/in-series from asynchronous baseline, orā€¦ ā€¢ Asynchronous out of pipeline for baseline/feedback for next dev cycle ā€¢ Notifications the way the team wants: Slack, email, report, dashboard, etc. ā€¢ Interrupt the pipeline the way the team wants: break the build, turn the merge button red, etc. ā€¢ Environment-specific (dev, staging, prod, etc.) ā€policyā€
  • 23. DevSecOps Tool recommendations ā€¢ SCA (aka dependency checkers, open source security scanners) are the best bang for the buck/effort. START HERE ā€¢ Next implement IAST or SAST (together, we created a category grouping these two called Primary Code Analysis). FAVOR IAST ā€¢ Embed in pipeline and treat like an additional test suite. ā€¢ For greenfield turn on all checkers and interrupt pipeline unless automated security tests come up clean. ā€¢ For legacy, ā€œstop the bleedingā€ by interrupting pipeline for NEW issues and slowly turn up the interrupt policy until all legacy issues are resolved. Plan to address all critical/high issues within 120 days.
  • 26. ā€¦ similar to what happened to QA Engineers with the Agile movement ā€¦ they will join a development team ā€¦ or they will become tool-smiths and advisors
  • 27. LinkedIn.com/in/LarryMaccherone Whatā€™s next? ā€¢ Questions? ā€¢ Read about the Trust Algorithm https://www.devsecopsdays.com/articles/ trust-algorithm-applied-to-devsecops ā€¢ Connect with me LinkedIn.com/in/LarryMaccherone