Summary:
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.
Topics discussed:
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
Learn more about Chris’ upcoming training opportunities:
Social
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...
BSidesHBG April 25
BSidesKC April 26
Possibly BSides Flood City (May 8) and BSides Ft Wayne (June 7) too
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