What happens when a covert entry specialist turns a Super Bowl hotel room into a rooftop breach point? Brent White, Sr. Principal Security Consultant & Covert Entry Specialist at Dark Wolf Solutions, offers Casey his approach to physical security testing that goes far beyond lock picking, rooted in understanding human psychology and building systematic infiltration strategies. Brent shares how his team compressed an entire backpack of penetration tools into a concealed-carry belt system that even works with swimming trunks. But the real breakthrough isn't in the gear — it's in his multi-day reconnaissance methodology that builds familiarity before attempting entry. Brent's "Post It flag" system transforms traditional physical assessments by having clients mark objects they're comfortable losing, leading to scenarios where his team wheels office chairs and $500 juice machines through bank lobbies while security guards helpfully watch their haul. This approach moves beyond simple "can you get in" to demonstrating real-world impact and exfiltration capabilities.  Topics discussed: Building familiarity through multi-day reconnaissance that establishes psychological comfort before entry attempts rather than relying on cold tailgating approaches. Transitioning from backpack-based toolkits to concealed carry belt systems that house bypass tools for major door configurations, American padlock bypasses, and dimple lock rakes. Mapping regional security culture patterns where Northeast locations show higher vigilance compared to South and Midwest willingness to help strangers. Using Proxmark readers and modified Flipper Zero devices hidden in Starbucks cups to capture badge credentials during natural conversations. Implementing hybrid covert-to-overt assessment methodology that escalates until detection then transitions to educational walkthroughs with clients. Developing systematic drone security evaluation frameworks that assess radio frequencies, web interfaces, payload access, and MAVLink flight data to identify pilot locations. Creating quick-change disguise systems using wig colors matched to facial hair combined with tactical clothing featuring concealed tool pockets. Establishing post-engagement flag collection strategies where clients mark acceptable-loss items, enabling teams to wheel office chairs and expensive equipment through lobbies as proof of exfiltration capability. Understanding how sUAS government standards are forcing commercial drone manufacturers to implement stronger security measures. Navigating destructive versus non-destructive entry protocols when clients approve hinge removal and window manipulation while avoiding classified room decertification that triggers 24/7 guard requirements. Listen to more episodes:  Apple  Spotify  YouTube Website