The cybersecurity landscape is evolving faster than ever, and Black Hat 2026 offered a front-row seat to the trends shaping the future of security. In this episode, host Kim Coombes is joined by Connection security experts John Chirillo, Rob Di Girolamo, and penetration testing specialist Joe Chmielewski to break down the event’s biggest announcements, research findings, and emerging security challenges.
Our expert panel explores how AI is transforming both attack and defense, why securing AI agents and machine identities is becoming a critical priority, and what organizations can learn from the latest advances in offensive security research. From AI-generated exploits and automated vulnerability discovery to autonomous security operations and identity protection, the discussion separates genuine innovation from industry hype while highlighting the practical actions security teams should take today.
Moderator: Kimberlee Coombes, Security Solution Architect, Connection
Guest: John Chirillo, Principal Security Architect, Connection
Guest: Rob Di Girolamo, Senior Security Architect, Connection
Guest: Joe Chmielewski III, Security Lead Systems Engineer, Connection
John Chirillo
John Chirillo is a Principal Security Consultant at Connection and a cybersecurity leader with more than 25 years of experience spanning security architecture, ethical hacking, managed security, risk, compliance, and emerging technologies. He holds numerous industry certifications, including CISSP, ISSAP, and CMMC Registered Practitioner, and has authored multiple books on cybersecurity and technology. John helps organizations translate complex security challenges into practical strategies that reduce risk and strengthen resilience. His current research and thought leadership focus on AI security, quantum readiness, offensive security, and preparing organizations for the next generation of cyber threats.
