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© 2019 Denim Group – All Rights Reserved
Building a world where technology is trusted.
The As, Bs, and Four Cs of
Testing Cloud-Native
Applications
1
September 12, 2019
Dan Cornell | CTO
© 2019 Denim Group – All Rights Reserved
Dan Cornell
• Founder and CTO of Denim Group
• Software developer by background
• OWASP San Antonio co-leader
• 20 years experience in software
architecture, development, and security
© 2019 Denim Group – All Rights Reserved
3
Advisory
Services
Assessmen
t Services
Remediation
Services
Vulnerability Resolution
Platform
Building a world where technology is trusted
How we can help:
Denim Group is solely focused on helping build
resilient software that will withstand attacks.
• Since 2001, helping secure software
• Development background
• Tools + services model
© 2019 Denim Group – All Rights Reserved
Agenda
• The Good Old Days
• The More Interesting New Days
• Architectural Bill of Materials
• Four Cs
• Reporting
• Tailoring
• Questions
4
© 2019 Denim Group – All Rights Reserved
The Good
Old Days
Blast it with SAST or DAST
Do some manual testing, and …
© 2019 Denim Group – All Rights Reserved
© 2019 Denim Group – All Rights Reserved
The More Interesting New Days
7
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The Even More Interesting New Days
8
© 2019 Denim Group – All Rights Reserved
A Dedicated Server at Rackspace?!
9
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What Changed?
10
© 2019 Denim Group – All Rights Reserved
An Aside: Why Did Things Change?
• Digital Transformation
• The “risk” we talk about is crap
• Falling behind creates existential risk for firms
• Must Go Faster?
• Change culture to DevOps
• Culture has changed to DevOps?
• Adopt new technologies to support mission
11
https://www.denimgroup.com/resources/whitepaper/security-the-other-side-of-digital-transformation/
© 2019 Denim Group – All Rights Reserved
What Changed?
• Architecture
• Monolithic -> Microservices
• Technology
• Cloud servers
• Cloud services
• Containers
• Serverless
• CI/CD Pipelines
12
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Microservices
If you couldn’t make one big thing work
properly, what makes you think you can
make thirty smaller things that need to talk
to one another work properly?
13
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How You Think Microservices
Will Work
14
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How Microservices
Actually Work
15
© 2019 Denim Group – All Rights Reserved
As, Bs, and Four Cs
• Architectural Bill of Materials
• Four Cs
• Code
• Components
• Compute
• Cloud Configuration
16
© 2019 Denim Group – All Rights Reserved
Software Bill of Materials (SBOM)
• What is
actually in the
software I am
shipping?
• Open source,
etc
17
OWASP Dependency Track
https://www.owasp.org/index.php/OWASP_Dependency_Track_Project
© 2019 Denim Group – All Rights Reserved
Architectural Bill of Materials
18
© 2019 Denim Group – All Rights Reserved
Architectural Bill of Materials
19
• What are the pieces of the system we are
looking at?
• Being able to answer:
• What are the various parts of the system?
• What do they consist of?
• What do they do?
• Where are they hosted?
© 2019 Denim Group – All Rights Reserved
Architectural Bill of Materials
20
• So a threat model?
• Yeah pretty much. A threat model.
© 2019 Denim Group – All Rights Reserved
High Level Threat Modeling
Concepts
Decide on
scope
1
Build your
dataflow
diagrams
2
Enumerate
threats
3
Decide on
mitigations
4
© 2019 Denim Group – All Rights Reserved
Creating Data
Flow Diagrams
(DFDs)
• Decompose
the system
into a series
of processes
and data
flows
• Explicitly
identify trust
boundaries
© 2019 Denim Group – All Rights Reserved
Example Data Flow Diagram
© 2019 Denim Group – All Rights Reserved
Identifying Threats from the
Data Flow
STRIDE is expansion
of the common CIA
threat types
• Confidentiality
• Integrity
• Availability
STRIDE
• Spoofing Identity
• Tampering with Data
• Repudiation
• Information
Disclosure
• Denial of Service
• Elevation of Privilege
© 2019 Denim Group – All Rights Reserved
Mapping Threats to Asset Types
Threat Type External
Interactor
Process Data Flow Data Store
S – Spoofing Yes Yes
T – Tampering Yes Yes Yes
R – Repudiation Yes Yes Yes
I – Information Disclosure Yes Yes Yes
D – Denial of Service Yes Yes Yes
E – Elevation of Privilege Yes
© 2019 Denim Group – All Rights Reserved
So What Does That Leave Us?
Take all the assets
Associate threat types with each asset
Voila! List of things we need to worry about
© 2019 Denim Group – All Rights Reserved
ABOM
• We at least need the results of Steps 1
and 2 to get our asset list and the
relationships
• May as well finish things off because we’ll
need the rest later on to provide context
for reporting
27
© 2019 Denim Group – All Rights Reserved
Given our ABOM
• We now need to look at the security of
each of the pieces in the overall system
• Test them for security issues at various
layers
• Aggregate the results
28
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Four Cs
29
Code
Components
Compute
Cloud Configuration
© 2019 Denim Group – All Rights Reserved
Code
30
© 2019 Denim Group – All Rights Reserved
Code
• This is the code you write
• Business logic
• Glue stuff together
• Traditional focus of OWASP/application
security
• Automated testing with SAST, DAST, IAST
• Manual penetration testing and code
review
31
© 2019 Denim Group – All Rights Reserved
Code – API Testing
• Great news – the DAST tools you
depended on for web application testing
might not work terribly well for APIs
• Some API-focused DAST tools
• OWASP ZAP has some capabilities in this
area
• Always option to do manual testing
32
© 2019 Denim Group – All Rights Reserved
Components
33
© 2019 Denim Group – All Rights Reserved
Components
• These are the open source components you include
so that you don’t have to write everything
• Libraries
• Frameworks
• Gained prominence with its introduction in the OWASP
Top 10 2013
• Gained notoriety with the Equifax breach
• Thanks, Struts…
• Test with Software Composition Analysis (SCA)
• Often need to manually validate impact
• Traditional SBOM scope
34
https://www.owasp.org/index.php/OWASP_Dependency_Check
© 2019 Denim Group – All Rights Reserved
Compute
35
© 2019 Denim Group – All Rights Reserved
Compute
• Something has to run all this code…
• Virtual machines, cloud servers,
containers
• Serverless takes this to the extreme
• Don’t forget dedicated servers
• Test with:
• Traditional vulnerability scanning
• Container scanning
36
© 2019 Denim Group – All Rights Reserved
Cloud Configuration
37
© 2019 Denim Group – All Rights Reserved
Cloud Configuration
• The squishiest of all the Cs
• Maybe that’s why it gets two Cs…
• Largely configuration checks
• Open S3 buckets
• Bad IAM set ups
• Will evolve over time
• If this presentation were being given a couple of years
ago, cloud servers might fall in this category
• Move stable stuff – cloud servers – into their own
Category
38
© 2019 Denim Group – All Rights Reserved
So What Does This All Look Like?
39
© 2019 Denim Group – All Rights Reserved
Reporting
• Know your audience(s)
• Who are you consumers?
• Security/risk management
• Individual service owners/developers
• Start with your ABOM to provide context
40
© 2019 Denim Group – All Rights Reserved
Security/Risk Management
• Risk = Impact x Likelihood
• Likelihood is important in these complicated systems
• DREAD
• CVSS vX – Base + Environmental Metrics
• Will often require a narrative
• ”If A, then B, then C…”
• Base concerns for exposure
• Compliance
• Service Level Agreements (SLAs)
41
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Service Owner/Developer
• Why should/must I care?
• How do I fix this?
42
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Tailoring to Your Requirements
• Nobody has the resources to do everything they
want
• If everything is important then nothing is important
• What services deal with the most critical data?
• What components of the system expose the most
risk?
• Are you more concerned that a container might have
a blank root password or that your login routine might
have Cross Site Scripting (XSS) exposed?
43
© 2019 Denim Group – All Rights Reserved
Prioritized Testing
44
• Dynamic testing of public-facing sites and
services
• That’s what most bad guys will see
• Cloud configuration checks to identify
potential unknown attack surface
• Open S3 buckets, etc
• Prioritize additional activities based on
resources
© 2019 Denim Group – All Rights Reserved
Tailoring to Your Requirements
45
© 2019 Denim Group – All Rights Reserved
Decisions You Might Make
• What’s the attack surface?
• Definitely known:
• Web front end
• Chat server
• Hosted MongoDB
• Need to determine additional exposure:
• Scan exposed network assets
• Check cloud configuration
46
© 2019 Denim Group – All Rights Reserved
Test Plan
• Enumerate assets to establish ABOM
• Cloud configuration check
• Identify S3 buckets, gross IAM sins
• Network scan of exposed (and owned) IPs
• DAST scan of Web Front End
• Maybe some manual penetration testing
• DAST/API scan of Chat Server
• Again maybe some manual penetration
testing
47
© 2019 Denim Group – All Rights Reserved
If You Have More Resources
• More manual testing for Web Front End and Chat
Server
• DAST/API scans of User/Content/Location
Services
• SAST and manual code review for Web Front End,
and User/Content/Location Services
• Interior network scanning
• Container vulnerability scanning for container
images running User/Content/Location Services
• Vendor security checks for hosted MongoDB
48
© 2019 Denim Group – All Rights Reserved
Building a world where technology is trusted.
@denimgroup
www.denimgroup.com
Dan Cornell
@danielcornell
www.denimgroup.com
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The As, Bs, and Four Cs of Testing Cloud-Native Applications

  • 1. © 2019 Denim Group – All Rights Reserved Building a world where technology is trusted. The As, Bs, and Four Cs of Testing Cloud-Native Applications 1 September 12, 2019 Dan Cornell | CTO
  • 2. © 2019 Denim Group – All Rights Reserved Dan Cornell • Founder and CTO of Denim Group • Software developer by background • OWASP San Antonio co-leader • 20 years experience in software architecture, development, and security
  • 3. © 2019 Denim Group – All Rights Reserved 3 Advisory Services Assessmen t Services Remediation Services Vulnerability Resolution Platform Building a world where technology is trusted How we can help: Denim Group is solely focused on helping build resilient software that will withstand attacks. • Since 2001, helping secure software • Development background • Tools + services model
  • 4. © 2019 Denim Group – All Rights Reserved Agenda • The Good Old Days • The More Interesting New Days • Architectural Bill of Materials • Four Cs • Reporting • Tailoring • Questions 4
  • 5. © 2019 Denim Group – All Rights Reserved The Good Old Days Blast it with SAST or DAST Do some manual testing, and …
  • 6. © 2019 Denim Group – All Rights Reserved
  • 7. © 2019 Denim Group – All Rights Reserved The More Interesting New Days 7
  • 8. © 2019 Denim Group – All Rights Reserved The Even More Interesting New Days 8
  • 9. © 2019 Denim Group – All Rights Reserved A Dedicated Server at Rackspace?! 9
  • 10. © 2019 Denim Group – All Rights Reserved What Changed? 10
  • 11. © 2019 Denim Group – All Rights Reserved An Aside: Why Did Things Change? • Digital Transformation • The “risk” we talk about is crap • Falling behind creates existential risk for firms • Must Go Faster? • Change culture to DevOps • Culture has changed to DevOps? • Adopt new technologies to support mission 11 https://www.denimgroup.com/resources/whitepaper/security-the-other-side-of-digital-transformation/
  • 12. © 2019 Denim Group – All Rights Reserved What Changed? • Architecture • Monolithic -> Microservices • Technology • Cloud servers • Cloud services • Containers • Serverless • CI/CD Pipelines 12
  • 13. © 2019 Denim Group – All Rights Reserved Microservices If you couldn’t make one big thing work properly, what makes you think you can make thirty smaller things that need to talk to one another work properly? 13
  • 14. © 2019 Denim Group – All Rights Reserved How You Think Microservices Will Work 14
  • 15. © 2019 Denim Group – All Rights Reserved How Microservices Actually Work 15
  • 16. © 2019 Denim Group – All Rights Reserved As, Bs, and Four Cs • Architectural Bill of Materials • Four Cs • Code • Components • Compute • Cloud Configuration 16
  • 17. © 2019 Denim Group – All Rights Reserved Software Bill of Materials (SBOM) • What is actually in the software I am shipping? • Open source, etc 17 OWASP Dependency Track https://www.owasp.org/index.php/OWASP_Dependency_Track_Project
  • 18. © 2019 Denim Group – All Rights Reserved Architectural Bill of Materials 18
  • 19. © 2019 Denim Group – All Rights Reserved Architectural Bill of Materials 19 • What are the pieces of the system we are looking at? • Being able to answer: • What are the various parts of the system? • What do they consist of? • What do they do? • Where are they hosted?
  • 20. © 2019 Denim Group – All Rights Reserved Architectural Bill of Materials 20 • So a threat model? • Yeah pretty much. A threat model.
  • 21. © 2019 Denim Group – All Rights Reserved High Level Threat Modeling Concepts Decide on scope 1 Build your dataflow diagrams 2 Enumerate threats 3 Decide on mitigations 4
  • 22. © 2019 Denim Group – All Rights Reserved Creating Data Flow Diagrams (DFDs) • Decompose the system into a series of processes and data flows • Explicitly identify trust boundaries
  • 23. © 2019 Denim Group – All Rights Reserved Example Data Flow Diagram
  • 24. © 2019 Denim Group – All Rights Reserved Identifying Threats from the Data Flow STRIDE is expansion of the common CIA threat types • Confidentiality • Integrity • Availability STRIDE • Spoofing Identity • Tampering with Data • Repudiation • Information Disclosure • Denial of Service • Elevation of Privilege
  • 25. © 2019 Denim Group – All Rights Reserved Mapping Threats to Asset Types Threat Type External Interactor Process Data Flow Data Store S – Spoofing Yes Yes T – Tampering Yes Yes Yes R – Repudiation Yes Yes Yes I – Information Disclosure Yes Yes Yes D – Denial of Service Yes Yes Yes E – Elevation of Privilege Yes
  • 26. © 2019 Denim Group – All Rights Reserved So What Does That Leave Us? Take all the assets Associate threat types with each asset Voila! List of things we need to worry about
  • 27. © 2019 Denim Group – All Rights Reserved ABOM • We at least need the results of Steps 1 and 2 to get our asset list and the relationships • May as well finish things off because we’ll need the rest later on to provide context for reporting 27
  • 28. © 2019 Denim Group – All Rights Reserved Given our ABOM • We now need to look at the security of each of the pieces in the overall system • Test them for security issues at various layers • Aggregate the results 28
  • 29. © 2019 Denim Group – All Rights Reserved Four Cs 29 Code Components Compute Cloud Configuration
  • 30. © 2019 Denim Group – All Rights Reserved Code 30
  • 31. © 2019 Denim Group – All Rights Reserved Code • This is the code you write • Business logic • Glue stuff together • Traditional focus of OWASP/application security • Automated testing with SAST, DAST, IAST • Manual penetration testing and code review 31
  • 32. © 2019 Denim Group – All Rights Reserved Code – API Testing • Great news – the DAST tools you depended on for web application testing might not work terribly well for APIs • Some API-focused DAST tools • OWASP ZAP has some capabilities in this area • Always option to do manual testing 32
  • 33. © 2019 Denim Group – All Rights Reserved Components 33
  • 34. © 2019 Denim Group – All Rights Reserved Components • These are the open source components you include so that you don’t have to write everything • Libraries • Frameworks • Gained prominence with its introduction in the OWASP Top 10 2013 • Gained notoriety with the Equifax breach • Thanks, Struts… • Test with Software Composition Analysis (SCA) • Often need to manually validate impact • Traditional SBOM scope 34 https://www.owasp.org/index.php/OWASP_Dependency_Check
  • 35. © 2019 Denim Group – All Rights Reserved Compute 35
  • 36. © 2019 Denim Group – All Rights Reserved Compute • Something has to run all this code… • Virtual machines, cloud servers, containers • Serverless takes this to the extreme • Don’t forget dedicated servers • Test with: • Traditional vulnerability scanning • Container scanning 36
  • 37. © 2019 Denim Group – All Rights Reserved Cloud Configuration 37
  • 38. © 2019 Denim Group – All Rights Reserved Cloud Configuration • The squishiest of all the Cs • Maybe that’s why it gets two Cs… • Largely configuration checks • Open S3 buckets • Bad IAM set ups • Will evolve over time • If this presentation were being given a couple of years ago, cloud servers might fall in this category • Move stable stuff – cloud servers – into their own Category 38
  • 39. © 2019 Denim Group – All Rights Reserved So What Does This All Look Like? 39
  • 40. © 2019 Denim Group – All Rights Reserved Reporting • Know your audience(s) • Who are you consumers? • Security/risk management • Individual service owners/developers • Start with your ABOM to provide context 40
  • 41. © 2019 Denim Group – All Rights Reserved Security/Risk Management • Risk = Impact x Likelihood • Likelihood is important in these complicated systems • DREAD • CVSS vX – Base + Environmental Metrics • Will often require a narrative • ”If A, then B, then C…” • Base concerns for exposure • Compliance • Service Level Agreements (SLAs) 41
  • 42. © 2019 Denim Group – All Rights Reserved Service Owner/Developer • Why should/must I care? • How do I fix this? 42
  • 43. © 2019 Denim Group – All Rights Reserved Tailoring to Your Requirements • Nobody has the resources to do everything they want • If everything is important then nothing is important • What services deal with the most critical data? • What components of the system expose the most risk? • Are you more concerned that a container might have a blank root password or that your login routine might have Cross Site Scripting (XSS) exposed? 43
  • 44. © 2019 Denim Group – All Rights Reserved Prioritized Testing 44 • Dynamic testing of public-facing sites and services • That’s what most bad guys will see • Cloud configuration checks to identify potential unknown attack surface • Open S3 buckets, etc • Prioritize additional activities based on resources
  • 45. © 2019 Denim Group – All Rights Reserved Tailoring to Your Requirements 45
  • 46. © 2019 Denim Group – All Rights Reserved Decisions You Might Make • What’s the attack surface? • Definitely known: • Web front end • Chat server • Hosted MongoDB • Need to determine additional exposure: • Scan exposed network assets • Check cloud configuration 46
  • 47. © 2019 Denim Group – All Rights Reserved Test Plan • Enumerate assets to establish ABOM • Cloud configuration check • Identify S3 buckets, gross IAM sins • Network scan of exposed (and owned) IPs • DAST scan of Web Front End • Maybe some manual penetration testing • DAST/API scan of Chat Server • Again maybe some manual penetration testing 47
  • 48. © 2019 Denim Group – All Rights Reserved If You Have More Resources • More manual testing for Web Front End and Chat Server • DAST/API scans of User/Content/Location Services • SAST and manual code review for Web Front End, and User/Content/Location Services • Interior network scanning • Container vulnerability scanning for container images running User/Content/Location Services • Vendor security checks for hosted MongoDB 48
  • 49. © 2019 Denim Group – All Rights Reserved Building a world where technology is trusted. @denimgroup www.denimgroup.com Dan Cornell @danielcornell www.denimgroup.com Questions and Answers