In this episode of Exploring Information Security, Tim chats with Chris Traynor of Black Hills Information Security (BHIS) and Ridgeback InfoSec. Chris is a seasoned penetration tester and educator who’s been developing hands-on training that’s grounded in real-world experience. He shares the origins of his “Offensive Tooling” classes, what makes a great pentest report, and how he balances teaching with travel, work, and family life.

Chris breaks down the tooling that matters, how he approaches infrastructure setup for operators, and why he emphasizes actionable reporting. He also talks about the importance of open-source tooling, customizing workflows, and automating the tedious parts of testing. Whether you're just getting into offensive security or are a veteran red teamer, this episode offers insights and practical takeaways.

• The importance of hands-on offensive tooling training

• How to write reports that are actually useful to dev and ops teams

• Why pentesters need infrastructure knowledge

• Open-source tools, custom scripts, and automation

• The challenges and wins of presenting at BSides and beyond

• Avoiding burnout while building community and sharing knowledge

Social

• Twitter

• LinkedIn

Upcoming Events

• March 28 security live on https://www.twitch.tv/womaninredpresents

• KernelCon April 1-2 teaching my Offensive Tooling for Operators 2-day class

• The Illustrated Pentester - Short Stories of Security Vol. 4 April 10

 - Past ones...

•    The Illustrated Pentester - Short Stories of Security

  • The Illustrated Pentester - Short Stories of Security Vol. 2

  • The Illustrated Pentester - Short Stories of Security Vol. 3

•  BSidesHBG April 25

•  BSidesKC April 26

•  Possibly BSides Flood City (May 8) and BSides Ft Wayne (June 7) too

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