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AppSec in a World of Digital Transformation
Presented by, John Dickson
© 2019 Denim Group – All Rights Reserved
Building a world where technology is trusted.
AppSec in a World of Digital
Transformation
John B. Dickson, CISSP #4649
Principal, Denim Group
@johnbdickson
© 2019 Denim Group – All Rights Reserved
Overview
• Digital Transformation Defined
• The Business Imperative to Move Faster
• The Opportunity for Security
• Security in This New World
© 2019 Denim Group – All Rights Reserved
My Background
• Ex-USAF & KPMG Security
• Application Security Enthusiast
• Helps CSO’s and CISO’s with AppSec
Programs
• ISSA Distinguished Fellow
• Security Author and Speaker
• MBA & Entrepreneur
© 2019 Denim Group – All Rights Reserved
The Delivery Platform
Central Resolution Hub Accelerate
Remediation
THREADFIX
ADVISORY
SERVICES
MANAGED
SERVICES
Application Testing
Quantifies Risk Across the Application
Portfolio
DevOps & AppSec
Transformation Consulting
Denim Group Overview
© 2019 Denim Group – All Rights Reserved
Disclosure Statement
• I don’t like the term “digital transformation”
© 2019 Denim Group – All Rights Reserved
The “Other Side” of Digital
Transformation
• IT and Security is on the Receiving End of
Digital Transformation
© 2019 Denim Group – All Rights Reserved
Tale of Two Rental Car
Experiences
© 2019 Denim Group – All Rights Reserved
Story #1: Pleasant Customer
Experience
© 2019 Denim Group – All Rights Reserved
Story #2: Customer Dumpster
Fire
© 2019 Denim Group – All Rights Reserved
Me
Reservation
System
Fleet Management
System
Car
Story #2: Dumpster Fire Backend
© 2019 Denim Group – All Rights Reserved
Digital Initiatives
• Business wants instant features and functions
• Pressure to push products to services to the market faster with a better
customer experience
• Time to market beats many other considerations
• Heavy use of user behavior analytics to customize buying experience
• Customers are becoming better at appreciating “goodness”
© 2019 Denim Group – All Rights Reserved
What This Means for You
• Rollout of new features measured in days
& weeks, not months
• Connected systems throughout the
organization
• Organizational changes are accelerating
• Security might be a consideration, but
time-to-market considerations are
paramount
© 2019 Denim Group – All Rights Reserved
Entire Tech Stack Changing
• Microservices
• Serverless Applications
• New(er) Languages & Frameworks
• All via CI/CD Pipelines
© 2019 Denim Group – All Rights Reserved
Gary McGraw, PhD.
Seven Touchpoints for Software
Security
© 2019 Denim Group – All Rights Reserved
One-Size-Fits-All Assembly Line
AppSec
© 2019 Denim Group – All Rights Reserved
Dirty Truth of AppSec
• Most appsec automation was optimized for
web applications written in compiled
languages
• Many WAFs are still pure layer 7 logging
devices
• Automated scanning coverage was never
great
• Most organizations never got near 100%
testing coverage
© 2019 Denim Group – All Rights Reserved
Modernize Approach to
Application Assessments
• Tune automation to technology stack you
are implementing
• Beef up compensating approaches where
automation comes up short
• Accelerate threat modeling
• Include as much testing in CI/CD pipeline
as tolerated
• Worry more about trust
• Be mindful of where your app lands
© 2019 Denim Group – All Rights Reserved
Provide AppDev Team with Security-
Annotated Cloud Reference Architecture
• On-prem security controls no longer exists
- Not all developers have got this memo!
• So where it lands matters
- Assume mixture of on prem/off prem clouds
• Absent of prescriptive guidance, expect
devs to ”roll their own”
© 2019 Denim Group – All Rights Reserved
Streamline Threat Modeling
Practices
• Threat modeling guides future dev far
more than testing
• Threat modeling might be more important
as automated test coverage is sketchier
• Knowing trust boundaries more important
given where app lands
© 2019 Denim Group – All Rights Reserved
Help Dev Teams Build Pipelines
with Security Baked in
• Understand trade-offs of time/depth of
testing
- Understand what you’re getting and not getting
• Develop alternative dual-track testing
models
• Iterative & tweak pipeline designs
© 2019 Denim Group – All Rights Reserved
Key Takeaways
• Digital Transformation + Tech Stack
Change = AppSec reset
• This change represents an opportunity to
further security interests
• If not you, you risk recreating the legacy
problems you inherited
© 2019 Denim Group – All Rights Reserved
Building a world where technology is trusted.
@denimgroup
www.denimgroup.com
@johnbdickson

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AppSec in a World of Digital Transformation

  • 1. © 2019 Denim Group – All Rights Reserved Thanks for joining our webinar! We will begin shortly. AppSec in a World of Digital Transformation Presented by, John Dickson
  • 2. © 2019 Denim Group – All Rights Reserved Building a world where technology is trusted. AppSec in a World of Digital Transformation John B. Dickson, CISSP #4649 Principal, Denim Group @johnbdickson
  • 3. © 2019 Denim Group – All Rights Reserved Overview • Digital Transformation Defined • The Business Imperative to Move Faster • The Opportunity for Security • Security in This New World
  • 4. © 2019 Denim Group – All Rights Reserved My Background • Ex-USAF & KPMG Security • Application Security Enthusiast • Helps CSO’s and CISO’s with AppSec Programs • ISSA Distinguished Fellow • Security Author and Speaker • MBA & Entrepreneur
  • 5. © 2019 Denim Group – All Rights Reserved The Delivery Platform Central Resolution Hub Accelerate Remediation THREADFIX ADVISORY SERVICES MANAGED SERVICES Application Testing Quantifies Risk Across the Application Portfolio DevOps & AppSec Transformation Consulting Denim Group Overview
  • 6. © 2019 Denim Group – All Rights Reserved Disclosure Statement • I don’t like the term “digital transformation”
  • 7. © 2019 Denim Group – All Rights Reserved The “Other Side” of Digital Transformation • IT and Security is on the Receiving End of Digital Transformation
  • 8. © 2019 Denim Group – All Rights Reserved Tale of Two Rental Car Experiences
  • 9. © 2019 Denim Group – All Rights Reserved Story #1: Pleasant Customer Experience
  • 10. © 2019 Denim Group – All Rights Reserved Story #2: Customer Dumpster Fire
  • 11. © 2019 Denim Group – All Rights Reserved Me Reservation System Fleet Management System Car Story #2: Dumpster Fire Backend
  • 12. © 2019 Denim Group – All Rights Reserved Digital Initiatives • Business wants instant features and functions • Pressure to push products to services to the market faster with a better customer experience • Time to market beats many other considerations • Heavy use of user behavior analytics to customize buying experience • Customers are becoming better at appreciating “goodness”
  • 13. © 2019 Denim Group – All Rights Reserved What This Means for You • Rollout of new features measured in days & weeks, not months • Connected systems throughout the organization • Organizational changes are accelerating • Security might be a consideration, but time-to-market considerations are paramount
  • 14. © 2019 Denim Group – All Rights Reserved Entire Tech Stack Changing • Microservices • Serverless Applications • New(er) Languages & Frameworks • All via CI/CD Pipelines
  • 15. © 2019 Denim Group – All Rights Reserved Gary McGraw, PhD. Seven Touchpoints for Software Security
  • 16. © 2019 Denim Group – All Rights Reserved One-Size-Fits-All Assembly Line AppSec
  • 17. © 2019 Denim Group – All Rights Reserved Dirty Truth of AppSec • Most appsec automation was optimized for web applications written in compiled languages • Many WAFs are still pure layer 7 logging devices • Automated scanning coverage was never great • Most organizations never got near 100% testing coverage
  • 18. © 2019 Denim Group – All Rights Reserved Modernize Approach to Application Assessments • Tune automation to technology stack you are implementing • Beef up compensating approaches where automation comes up short • Accelerate threat modeling • Include as much testing in CI/CD pipeline as tolerated • Worry more about trust • Be mindful of where your app lands
  • 19. © 2019 Denim Group – All Rights Reserved Provide AppDev Team with Security- Annotated Cloud Reference Architecture • On-prem security controls no longer exists - Not all developers have got this memo! • So where it lands matters - Assume mixture of on prem/off prem clouds • Absent of prescriptive guidance, expect devs to ”roll their own”
  • 20. © 2019 Denim Group – All Rights Reserved Streamline Threat Modeling Practices • Threat modeling guides future dev far more than testing • Threat modeling might be more important as automated test coverage is sketchier • Knowing trust boundaries more important given where app lands
  • 21. © 2019 Denim Group – All Rights Reserved Help Dev Teams Build Pipelines with Security Baked in • Understand trade-offs of time/depth of testing - Understand what you’re getting and not getting • Develop alternative dual-track testing models • Iterative & tweak pipeline designs
  • 22. © 2019 Denim Group – All Rights Reserved Key Takeaways • Digital Transformation + Tech Stack Change = AppSec reset • This change represents an opportunity to further security interests • If not you, you risk recreating the legacy problems you inherited
  • 23. © 2019 Denim Group – All Rights Reserved Building a world where technology is trusted. @denimgroup www.denimgroup.com @johnbdickson