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Pen Testing with Iron

Pen Testing with Iron. Andrew Wilson Trustwave SpiderLabs. Ubiquitous Hello. Application Security Consultant Ex-Software Developer– Microsoft MVP Long walks on the beach Dancing in the rain. Goals. Why Bother? Introduction to the DLR & CLR Getting Running Examples:

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Pen Testing with Iron

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  1. Pen Testing with Iron • Andrew Wilson • Trustwave SpiderLabs

  2. Ubiquitous Hello • Application Security Consultant • Ex-Software Developer– Microsoft MVP • Long walks on the beach • Dancing in the rain

  3. Goals • Why Bother? • Introduction to the DLR & CLR • Getting Running • Examples: • Reflection and Disassembly • Leveraging Existing Tools • Driving Applications with Scripts

  4. Why Bother? • Best of Both Worlds • Deeper Reach • Simplification

  5. Python & Ruby: • Make Developers Security Testers Happy! • Awesome at Scripting & Interactive Development (read: rapid prototyping) • Incapable (normally) of interaction with .NET 

  6. .NET Framework Is: • Awesome in library, connectivity, and tooling • Commonly used by companies you test • Sucky at scripting and interactive programming

  7. CLR <3 • Focuses concerns against business problems • Handles: • Memory Management • Metadata • JIT • Common Type System

  8. DLR <3

  9. Expression Trees • Translate code from one language to MSIL • Introduced in .Net 3.5 via Linq

  10. DLR+CLR • Peace Love & Harmony • Bi-Directional support: • DLR – CLR (Ex. Python – CLR) • CLR – DLR (Ex. CLR – Embedded Python)

  11. IronPython • Significantly more mature (circa 2006) • Better support for existing Python applications • Loads apps by being manually added to lib

  12. IronRuby • Needs your support • Just obtained Visual Studio Support • Loads assemblies via igem (instead of gem) install <gem>

  13. Getting Started • You will need: • IronRuby OR IronPython • Language tools are optional • Visual Studio Express OR MonoDevelop • Reflector

  14. Use Cases: • Disassembly / Reflection • Existing Tooling • Driving Applications via Scripts

  15. No Disassemble!

  16. Reflection::noitcelfeR • .NET has reflection– but it sucks • Ruby has reflection– and it rules • Always Cheat, Always win.

  17. Use Existing Tools

  18. Use Existing Tools • Some things aren‘t 100% supported • Workarounds are in progress & inevitable • Gains are still decent & getting better

  19. THE POWER OF GRAYSKULL!!

  20. When Not To Use: • When You Can’t • Testing Web Applications You Can Debug Natively • When Native Tools Are Better

  21. Closing Thoughts • No Free Lunches • Offers Unique Opportunities • Projects In Transition

  22. QA

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