Hacker in the Loop (formerly Simply Offensive)

What happens when AI moves beyond answering pentesting questions and starts actively participating in the testing workflow?

In this episode of Hacker in the Loop, Phillip Wylie is joined by his colleague Jacob Krell for a hands-on look at building an agentic hacking harness using Cursor, Metasploit, MCPs, AI models, and custom guardrails. Jacob walks through the process in real time, showing how an AI-powered environment can research techniques, build tools, maintain engagement state, execute testing workflows, troubleshoot problems, and help a penetration tester work significantly faster.

Rather than treating AI as a replacement for the penetration tester, the discussion focuses on using it as an acceleration layer. Jacob demonstrates how a properly designed harness can handle repetitive testing activities while leaving the human operator responsible for direction, judgment, and higher-value investigation.

GitHub for Metasploit Cursor Harness: https://github.com/Suzu-Testing/metasploit-cursor-harness

Connect with Jacob Krell:

LinkedIn: ⁠https://www.linkedin.com/in/jacob-krell/⁠⁠

X: https://x.com/hackerfren

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

YouTube: https://youtube.com/@PhillipWylie

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Presented by Suzu Labs

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All the ways to connect with @Suzulabs

https://suzulabs.com

https://x.com/suzulabs

https://www.linkedin.com/company/suzu-labs/

What does it take to build one of DEF CON's largest and most popular villages?In this episode of Simply Offensive, Phillip Wylie sits down with Rachael Tubbs, PhD, Research Director at Independent Security Evaluators (ISE) and one of the leaders behind IoT Village, to discuss the evolution of one of the cybersecurity community's favorite DEF CON attractions.From Bluetooth-enabled toilet seats and connected litter boxes to IoT security research, hacker psychology, and advice for first-time DEF CON attendees, this conversation offers an inside look at how IoT Village has grown into a global educational initiative that helps thousands of security professionals develop hands-on skills every year.Whether you're attending DEF CON for the first time or you're an experienced hacker looking for your next challenge, this episode highlights why IoT Village continues to be a must-visit destination.

Connect with Rachael Tubbs:

LinkedIn: https://www.linkedin.com/in/dr-rachael-tubbs-1a1085135/

IoT Village: https://iotvillage.org/

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie

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Presented by Suzu Labs

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All the ways to connect with @Suzulabs

https://suzulabs.com

https://x.com/suzulabs

https://www.linkedin.com/company/suzu-labs/

Artificial intelligence is transforming offensive security, but does that mean traditional penetration testing skills are becoming obsolete? In this episode of Simply Offensive, Phillip Wylie is joined by offensive security researcher Milton "wetw0rk" Valencia and Suzu Labs offensive security practitioner Jacob Krell for an in-depth discussion about the future of penetration testing, exploit development, and the role AI is playing in modern offensive security. Drawing from decades of combined experience, the conversation explores why understanding the underlying fundamentals remains essential—even as AI dramatically accelerates many offensive security workflows. From exploit development and malware research to certifications, training philosophies, and the economics of cybersecurity consulting, the panel examines what the next generation of ethical hackers needs to succeed. Milton shares insights from years of exploit development and red team operations, including lessons learned at IBM, Immunity, and HPE, while Jacob discusses his research into AI-assisted penetration testing and how large language models are changing the speed and scale of offensive security work.

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Connect with Milton Valencia:

LinkedIn: https://www.linkedin.com/in/milton-wetw0rk/Blog: GitHub: https://wetw0rk.github.io/

YouTube: https://www.youtube.com/ ⁨@wetw0rk7⁩  =========================

Connect with Jacob Krell:LinkedIn: ⁠https://www.linkedin.com/in/jacob-krell/⁠⁠

X: https://x.com/hackerfren

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Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie

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Presented by Suzu Labs

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All the ways to connect with @Suzulabshttps://suzulabs.com

https://x.com/suzulabs

https://www.linkedin.com/company/suzu-labs/

In this episode of Simply Offensive, Phillip Wylie welcomes Katherine (Kat) McNamara, Technical Solutions Architect at Cisco and holder of two prestigious Cisco Certified Internetwork Expert (CCIE) certifications. Kat shares her remarkable journey from overcoming significant personal challenges to becoming one of the industry's leading networking and security professionals.The conversation explores the evolution of cybersecurity careers, the value of certifications versus degrees, today's hiring landscape, and the growing influence of AI on offensive and defensive security. Phillip and Kat also examine why organizations continue to struggle with AI security, the dangers of "vibe coding," and how organizations can avoid repeating the same mistakes made during the early cloud adoption era.Whether you're an aspiring cybersecurity professional or an experienced practitioner navigating AI-driven security challenges, this episode delivers practical insights, honest perspectives, and plenty of thought-provoking discussion.

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Connect with KatherineMcnamara:

LinkedIn: https://www.linkedin.com/in/katherinermcnamara/

X: https://x.com/kmcnam1

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

YouTube: https://youtube.com/@PhillipWylie

X: https://x.com/phillipwylie

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Presented by Suzu Labs

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All the ways to connect with @Suzulabs

https://suzulabs.com

https://x.com/suzulabs

https://www.linkedin.com/company/suzu-labs/

In this episode of Simply Offensive, Phillip Wylie sits down with longtime friend, former coworker, and cybersecurity professional Darin Fredde. The conversation traces Darin's journey from computer-aided design and telecommunications to becoming a CIO, security architect, penetration tester, and AI advocate. Along the way, Darin shares lessons learned from decades in technology, how curiosity helped him succeed in offensive security, and why embracing AI is essential for today's cybersecurity professionals. 

In this episode of Simply Offensive, Phillip Wylie sits down with longtime friend, former coworker, and cybersecurity professional Darin Fredde. The conversation traces Darin's journey from computer-aided design and telecommunications to becoming a CIO, security architect, penetration tester, and AI advocate. Along the way, Darin shares lessons learned from decades in technology, how curiosity helped him succeed in offensive security, and why embracing AI is essential for today's cybersecurity professionals.

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Connect with Darin Fredde:

https://www.linkedin.com/in/darinfredde/

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

YouTube: https://youtube.com/@PhillipWylie

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Presented by Suzu Labs

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All the ways to connect with @Suzulabs

https://suzulabs.com

https://x.com/suzulabs

https://www.linkedin.com/company/suzu-labs/

In this episode of Simply Offensive, Phillip Wylie sits down with longtime cybersecurity professional Jim Nitterauer to discuss his unconventional journey from environmental microbiology researcher to entrepreneur, infrastructure engineer, security leader, and CISO. Jim shares lessons learned from building one of the early web hosting companies in the Southeast, helping scale security services at AppRiver, leading compliance and security programs through acquisitions, and navigating the rapidly evolving world of AI.The conversation explores practical AI adoption, security leadership, DNS fundamentals, career resilience, and why cybersecurity professionals should focus on mastering the basics before chasing the latest technology trends.Connect with Jim Nitterauer:https://www.linkedin.com/in/jnitterauer/=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Presented by Suzu Labs=========================All the ways to connect with @Suzulabs

https://suzulabs.comhttps://x.com/suzulabshttps://www.linkedin.com/company/suzu-labs/

In this episode of Simply Offensive, Phillip Wylie sits down with V, a longtime contributor to the Dallas cybersecurity community, board member for B-Sides DFW, and cybersecurity professional with experience spanning Identity and Access Management (IAM), Governance, Risk, and Compliance (GRC), third-party risk management, and security program development. Together they discuss alternative paths into cybersecurity, the importance of networking, the value of community involvement, and why not every cybersecurity career requires coding.

Connect with V Wixon:

LinkedIn: https://www.linkedin.com/in/victoriawixon/

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

YouTube: https://youtube.com/@PhillipWylie

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Presented by Suzu Labs

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All the ways to connect with @Suzulabs

https://suzulabs.com

https://x.com/suzulabs

https://www.linkedin.com/company/suzu-labs/

From Law Enforcement to Cyber Threat Intelligence: Andrew “GingerHacker” Crotty’s Journey into Cybersecurity

In this episode of Simply Offensive, Phillip Wylie sits down with Andrew “GingerHacker” Crotty to talk about breaking into cybersecurity, building a career in cyber threat intelligence (CTI), and creating content that helps others enter the industry. Andrew shares his unconventional path from law enforcement and military service into cybersecurity and explains how curiosity, persistence, and community shaped his success.

The conversation dives into what cyber threat intelligence actually looks like day to day, how CTI teams support incident response, and practical advice for professionals who want to pursue careers in intelligence, SOC operations, or offensive security. Andrew also discusses his YouTube channel and nonprofit efforts focused on helping newcomers break into cyber.

Connect with Andrew “GingerHacker” Crotty:

LinkedIn: https://www.linkedin.com/in/andrew-crotty-gingerhacker/

YouTube: https://www.youtube.com/channel/UCGX_oAbc0_CLEdwMI5n64oQ

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Connect with your host, Phillip Wylie:

LinkedIn: https://linkedin.com/in/phillipwylie

YouTube: https://youtube.com/@PhillipWylie

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Presented by Suzu Labs

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All the ways to connect with @Suzulabs

https://suzulabs.com

https://x.com/suzulabs

https://www.linkedin.com/company/suzu-labs/

In this episode of Simply Offensive, Phillip Wylie sits down with fellow Suzu Labs team member Steven Swift to discuss cybersecurity from a defensive and consulting perspective. Steven shares his journey from aspiring software developer to incident response specialist, consultant, and vCISO advisor working across security governance, AI, compliance, and enterprise risk management.The conversation explores how AI is reshaping cybersecurity, the challenges organizations face when implementing AI securely, and why phishing, shadow IT, and weak operational processes still remain some of the biggest risks facing organizations today. Steven also shares practical career advice for anyone trying to break into cybersecurity and explains why broad technical experience is one of the strongest foundations for long-term success.

=========================Connect with Steven Swift:LinkedIn: https://www.linkedin.com/in/steven-swift-5238956a/=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Presented by Suzu Labs=========================All the ways to connect with @Suzulabs

https://suzulabs.comhttps://x.com/suzulabshttps://www.linkedin.com/company/suzu-labs/

In this episode of Simply Offensive, Phillip Wylie sits down with Joff Thyer to unpack how artificial intelligence is reshaping cybersecurity. From the evolution of training and conferences to the rapid acceleration of vulnerability discovery, Joff shares hard-earned insights from decades in IT and offensive security.The conversation dives into the realities behind AI hype, where automation will replace repetitive pentesting tasks, and where human expertise still matters most. Joff also breaks down critical risks like non-human identity management and explains why fundamentals are more important than ever in an AI-driven world.=========================Connect with Joff Thyer:https://www.linkedin.com/in/joffthyer/=========================Connect with your host, Phillip Wylie:LinkedIn: https://linkedin.com/in/phillipwylieYouTube: https://youtube.com/@PhillipWylie=========================Presented by Suzu Labs=========================All the ways to connect with @Suzulabs

https://suzulabs.comhttps://x.com/suzulabshttps://www.linkedin.com/company/suzu-labs/