DevSecOps Boot Camp

Part 1: DevOps, Security, and DevSecOps: Definitions

1. DevOps
2. Security
3. Risk
4. Culture
5. Agility
6. Testing
7. Continuous Integration
8. Continuous Delivery

Part 2: Where do we start with security?

1. Risk review
2. Policy
3. Roles
4. Compliance, regulatory and GRC
5. The Pipeline Model
6. Exercise A: Value Stream Mapping

Part 3: Security as a DevOps practice

1. Traditional vs. “DevOps” security
2. Tools vs. processes
3. Security, not compliance
4. Prioritizing testing for risk
5. Reducing source code footprint
6. Static analysis for secure code
7. Feature toggles for security

• Toggle points
  • Toggle router
  • Toggle configuration

1. DevSecOps and technical debt management

Part 4: DevSecOps and “requirements”

1. Designing for security
2. Assessing risk appetite
3. Modeling threats
4. Product architecture
5. Use cases, antipatterns and abuse cases
6. Dataflows and trust boundaries
7. Exercise B: Threat Modeling

Part 5: Secure development patterns

1. Secure code overview
2. OWASP review
3. Tools for automating OWASP

• OWASP dependency checkers
  • OWASP Zap during regular functional tests

1. Developer guidelines & checklists
2. Tools to use
3. Coding Standards (top 5 languages)
4. Common pitfalls
5. Identifying Unsafe Code

Part 6: Security Testing in the Pipeline

1. Testing before commit
2. Scanning for secrets
3. Hook examples
4. Application security testing

• Static
  • Dynamic

1. Testing dependencies
2. How to treat manual testing
3. Performance Testing

• Testing for load
  • Testing for stress
  • Soak tests
  • Spike testing

1. Testing in parallel
2. Staging
3. Mutation testing and tools for performing it
4. User role testing

Part 7: Identity and Access Management (IAM)

1. IAM overview
2. Identity profiles
3. Using IAM for automation
4. IAM practices in the cloud
5. IAM as an application building block
6. IAM antipatterns
7. Guided discussion: IAM in a Microservices use case

Part 8: Deployment patterns for security

1. Canary candidates
2. Dark launches
3. Streamlining libraries and dependencies
4. Keeping packages up to date
5. Keeping deploys repeatable and reliable
6. OpenSCAP for scanning baselines before and after deployments
7. Scanning web server configuration
8. Database exploitation through applications
9. Infrastructure scanning

• OpenVAS
  • NMAP

1. Scanning web applications

• W3AF
  • Wapiti

Part 9: DevSecOps and Operations

1. Where does Ops security begin and end?
2. Infrastructure as Secure Code
3. Incident response planning and emergency drills
4. Release Archives
5. OS Protections:

• Address Space Layout Randomization
  • Non-Executable Stacks
  • W^X
  • Data Execution Prevention
  • SELinux

1. Monitoring, logging and intelligent alerts

• Splunk mini-tour: A transformative tool for analyzing machine data, operational risk, and application health

1. Log management
2. Penetration Testing
3. Exercise C: Profiling a DevSecOps Hybrid model

Part 10: Policy, Governance, and Audit

1. GRC review
2. Coding for compliance
3. DevOps and the “segregation of duties”
4. Tooling example: Chef InSpec
5. Change management and policy
6. Exercise D: Automated vs. Manual, to comply with Audit requirements

Part 11: Change management and DevSecOps

1. Three types of “change”
2. When and why to use CAB boards
3. Peer review vs. change management
4. Automating change management
5. ITIL in 2020

Part 12: Measurement and metrics

1. The core toolkit of metrics
2. The best way to institute alerts
3. Managing alerts
4. Proactive vs. reactive metrics
5. Measurement antipatterns

Part 13: More advice on the cultural factors

1. Security fails and breakdowns
2. Incentive, fear, and reward
3. Getting outside IT
4. How to shift left
5. Building security in
6. Cost and the business case for proactive security
7. Overcoming conventions of the past
8. Bridging silos – why and how
9. Exercise E: Rearranging incentives

Part 14: Putting it all together

1. Class recap and final questions
2. What will you do differently when you return to work?

• Anyone in an IT Leadership role
• CIOs / CTOs /CSO
• Security Administrators
• Any Security Staff
• System Administrators
• IT Operations Staff
• Release Engineers
• Configuration Managers
• Anyone involved with IT infrastructure
• Developers and Application Team leads
• ScrumMasters
• Software Managers and Team Leads
• IT Project & Program Managers
• Product Owners and Managers