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HouSecCon 2019: Offensive Security - Starting from Scratch


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HouSecCon 2019 Offensive Security - Starting from Scratch. Learn from Spencer Koch and Altaz Valani about how to build an offensive security program from scratch, incorporating application security, infrastructure vulnerability management, hardening, devsecops, security champions, and red teaming. Be able to organize these capabilities to tell a story and build maturity to help your organization be more secure. Includes gotchas and lessons learned from industry experience.

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HouSecCon 2019: Offensive Security - Starting from Scratch

  1. 1. Offensive Security Transformation: Starting from Scratch Spencer Koch Offensive Security Leader, Securimancy Altaz Valani Cyber Security Researcher, Security Compass
  2. 2. Who We Are Spencer Koch Offensive Security Leader @sp3nx0r Altaz Valani Cyber Security Researcher, Security Compass
  3. 3. This talk is: • Aimed at security leaders early on in the maturity curve • A cohesive storyboard for disparate capabilities that may already exist within SecOps teams • Pointers on what worked well and resources to start down this path • Both a practitioner and research perspective This talk is not: • Going to go deep in implementation or tooling details • Going to be news to anyone doing red teaming or having mature appsec capabilities About This Talk
  4. 4. How I structured my OffSec department: Application Security DevSecOps Security Champions Hardening Infra Vuln Management Red Team
  5. 5. You have inventories galore...? • Application listing • Infrastructure • Crown jewels / risk rankings / BIAs You have a Dev Team...? You have a Blue Team...? You have permission to fire...? • Buy-in from leadership • Know where the fragile network bits are You aren't a jerk...? Huge Assumptions
  6. 6. Application Security (Appsec) Overview Design Requirements Dependency Checking Source Code Analysis Dynamic App Testing Gray Matter Testing Require- ments Design Develop Build Test Deploy
  7. 7. • Doesn't work: Providing a long list of policies (be specific) • Begin with driving the right security requirements • Goal is traceable and reusable requirements into the DevOps pipeline • Don't start from scratch, fork and make your own • OWASP ASVS or NIST, pepper in regulatory reqs • Tie into your DevOps training • Establish de facto minimum standard against range of app architectures Design Requirements Design Requirements Dependency Checking Source Code Analysis Dynamic App Testing Gray Matter Testing
  8. 8. • One small step into the business world... • Eventually need to convert 'policy speak' to 'DevOps speak' • Agile stories? Microsoft SDL? Custom? • Create a "policy to execution" pipeline for scaling • For large orgs, eventually extend policy to execution into services layer Design Requirements Business Risk Policies mitigate d by Procedures enforced through
  9. 9. • Dependency management • Start here! Easy, cheap, gateway drug • Built in Github, OSS like OWASP Dependency Check, freemium Snyk • Frameworks need patching just OSes do, don't forget about them • Linters / Code Quality • Easy mode checks: dangerous/deprecated functions, simple regexes, easy analytics • Lots of devs think this is enough • Examples: SonarQube, TSLint Source Code Analysis Design Requirements Dependency Checking Source Code Analysis Dynamic App Testing Gray Matter Testing
  10. 10. • Dedicated security scanners, able to follow source to sink • Pay an arm/leg (money and resources) to get false positives • No one SAST to rule them all – and that's ok! • Give/take with UI, CI/CD integration, SaaS, languages, speed • Great SAST listing: static-analysis • Hardest problem? Sizing for licenses (how's that inventory) Source Code Analysis - SAST
  11. 11. • How are you pushing security defects to backlog? ALM Integrations • DO NOT PRINT TO PDF & CHUCK • Customize your own ruleset / criticality ranking • You will spend a lot of time here trying to get this right... Source Code Analysis Gotchas • Use those IDE integrations – devs don't want another tool
  12. 12. • Coding standards for the team: it should exist and include security topics! • Appsec team sets the structure (e.g. how to solve for input sanitization, output encoding, database interaction, authX, logging) • Dev teams fill in their language/framework specific ways of achieving these guidelines • Build secure libraries if devs' framework doesn't handle it! • Infrastructure as Code (IaC) also needs standards too • Leverage others' work! CERT, OWASP, something... Secure Coding Standards
  13. 13. • Build on what is already done today (peer review? self review? no review?) • Define what needs to be reviewed: security features, APIs, code dealing with money/PII, first-of code using new framework/design/etc.) at a minimum • Keep it short! Don't kill them with checklists... • Code review notes become training vehicle • Architectural design decisions vs. syntax Code Reviews including Security!
  14. 14. • Requires compiled code, comes later in SDLC cycle • Can be automated / integrated into CI/CD • Works via HTTP request/response - great for web/mobile apps & APIs • Catches a different & overlapping set of vulns from SAST • Fewer false positives, and triage effort generally less than SAST • What about WAF / virtual patching? Yep, do this... • What about IAST/RASP? Don't worry about it yet... Dynamic Application Testing (DAST) Design Requirements Dependency Checking Source Code Analysis Dynamic App Testing Gray Matter Testing
  15. 15. • Every PMs' favorite step, or AKA "where the greenlight happens” • Pentesting != Secure App <- culture change • Shifting security left is hard, so spin as security == quality • Don't waste resources on simple, repeatable tasks - save these folks for the "hard stuff": business logic, authX, session management, crypto • Go broad: systemic testing beyond the app (adversaries won't respect app boundaries), work top-down to provide contextual priority of vulns • Expensive to execute, expensive to fix defects, always timeboxed • Avoid RCP: pick a partner(s), pick a framework, get involved Gray Matter Testing Design Requirements Dependency Checking Source Code Analysis Dynamic App Testing Gray Matter Testing
  16. 16. • That's a lot of testing, so what's your plan? • Utilize a framework (OWASP SAMM 2.0?) and benchmark your progress • Don't lose focus while chasing maturity – learn from CMMI • This never ends – continual improvement, continual reassessment • Don't be afraid to add your own capabilities – remain relevant and look for what's critical for assurance to your business Appsec Framework
  17. 17. • Start small: • # of apps onboarded / total apps • Vulnerability type by time (SQLi, XSS, etc.) • Average time to remediation • Even those 3 can be hard • Focus on telling a story and grow • Stay away from # of vulns metrics, stick to behavior around those vulns Metrics
  18. 18. • if (!infra_vuln && !appsec): devsecops = doomed • DevSecOps Manifesto by Larry Macherone: Build security in more than bolt it on • All about about automating manual security testing processes • Make friends with DevOps, understand pipelines • Build at lab/home, follow along with Securing DevOps by Julien Vehent • With this understanding, where to start putting Sec in DevOps? DevSecOps – Getting Started
  19. 19. • SANS Secure DevOps Toolchain - epically good at framing your capability discussion! • Build a mindmap, add your priorities and start filling in blanks within your org • Be Agile just like the dev teams – iterate! • Keep it automated, reduce friction SANS Secure DevOps Toolchain
  20. 20. • Be choosey about what "breaks the build", start without any breaks • Plan out how security defects make it into the backlog: manual is painful • Get involved in backlog prioritization, don't be unreasonable • Come up with a plan and prioritize: ease to implement, bang for buck • Examples: dependency checking, to secrets scanning, to CIS benchmarks, to OWASP Top 10 DAST scanning, to … • Infra is always easier than app • Expect to have to code some stuff, get your hands dirty DevSecOps Gotchas
  21. 21. Don't be afraid of "bimodal DevSecOps": quick & dirty vs. deep-dive DevSecOps Gotchas CI/CD Integrated Testing •Focus on speed and keeping signal-to-noise ratio low •Completes in minutes, not days •Catch "heavy hitting" vulns (OWASP Top 10) Out-of-Band Testing •Scheduled on a frequency •Full code base, full URI path, full everything •Appsec engineer prunes false positives
  22. 22. • Devs will resist; too much on their plate already • Start with a respected developer interested in security • Designate as security champion and commit (not a part time role; needs budget & training) • Keep the momentum – it's change management (Kotter, PDCA, ..) • Get some wins (measurable ROI on pre/post prod vuln metrics) across different champions and build toward a SC program • Build word of mouth, sell career development for devs, success spreads • Not worth pursuing nay-sayers, let them get FOMO • Scale to a community of practice that offers advice, tools, onboarding, etc. Security Champions
  23. 23. • Work with your sysadmins, be reasonable, keep them happy • Where are you today? Start with CIS/NIST for core OSes, make the standards your own, document your deviations • You will have hundreds of findings at the beginning – don't panic, it's normal • Work the list - prioritize in phases, based on criticality and testing timing • After a few rounds, expand to less familiar platforms (middleware, cloud platforms, network gear) • Patterns will emerge, don't worry if there's no CIS benchmark for $STUFF Hardening - RHEL - Win2012
  24. 24. • Scan all the things – this is the easiest part of this talk • Don't trust your asset data, and add your results to IT asset data • Automate infrastructure scanning/validation and tie to risk tolerance for key applications (don't do this alone, get the business involved – they own risk register) • Infra vuln management is collaborative - understand impact to sysadmins and get their help to create the right processes and data • Infrastructure as Code gets devs involved too, codify your hardening/scanning Infra Vuln Management
  25. 25. • Frame your scan objectives: discovery, subnet/asset, agent • DON'T PRINT TO CSV – utilize best fix paths and pick reasonable goals • If you can't explain what the vuln is / how the vuln was detected, go research it • Sell to sysadmins as validation of patching/config, you're in it together! • Spot the patterns – don't forget about feedback loops Infra Vuln Management Gotchas
  26. 26. • Don't do this if you aren't doing basic infra vuln management, go focus on that • Focus on blue team effectiveness at the beginning • Visualize gaps and help Blue Team be better • Your reports have power – write each scenario up as a budget request Red Team
  27. 27. • Phishing activities • OSS tools galore like Gophish, just add AWS infrastructure • Social engineering • Call center password reset • Signature Emulation – is your $TOOL detecting what you think it does? • (Network) BT3 – Blue Team Training Toolkit / (Host) Red Canary • Active Directory health (Bloodhound / PingCastle) • Awesome Redteaming lists – pick your poison Red Team Introductory Activities
  28. 28. • Continue to build, automate where possible • See a technique on Twitter, try it out and see if Blue Team sees it Red Team Final Notes • Feedback loop forevah • Always focus on ROI and value proposition, or face budget cuts • Don't expect or try to be the next APT
  29. 29. Problem: Everything's going to the cloud! Oh nooooes… Approaches that work: • Fight for testing as it moves – you may never see that app again! • Shift security testing focus from depth to breadth • Change methodologies – don't be the blocker • Change the duration – 3 apps per week • Stress importance of risk registers and good documentation • Pick the hill(s) to die on – care about the most critical vulns Bonus: Cloud Migrations
  30. 30. Ditch FUD, embrace the new • Use Infrastructure as Code to your benefit • Use Cloud Service Provider tools to your benefit • Push for network segmentation • Encourage use of cloud devops tools – they're likely more secure than self-managed Hardest part of migration: getting funding to fix those uncovered vulns Bonus: Cloud Migrations - IaC hardening - CSP tooling for hardening/alerting
  31. 31. • Still a fledgling discipline, room to explore • Get involved with DevSecOps communities, local chapters • Partner with researchers • Industry collaboration - reach out to us! Next Steps / Where To Go From Here