Episode 103: YOLO Patching

Almost Ten years and 100+ episodes in, we reunite for a conversation that has nothing to do with prompts and everything to do with the infrastructure most of us still actually run. In this episode we're joined by Claudia Perez, who's spent the last several months leading a complex Windows 11 deployment and brings a refreshingly practical take on modern endpoint management. We dig into why Windows is far from dead, why identity and data - not the device - are where every modernization journey should start, and how to think about the messy reality of hybrid-joined environments still tethered to on-prem print servers, file shares, and legacy apps. In this episode we also dig into: * Why "identity is the new perimeter" should drive your endpoint strategy, not the other way around * The TPM/certificate refresh looming in June, and why proactive beats reactive (again) * The BitLocker bypass disclosure and rethinking how we protect local resources * Copilot on the PC: block it, embrace it, or protect the data and trust your users? * Why "the patches are coming" - AI-driven vulnerability discovery and whether ring-based deployment still holds up * Greenfield vs. brownfield: where to actually start, and why apps are the most underestimated piece of the puzzle A practical, occasionally irreverent conversation about maturing the basics — patching, management, identity - for the real world of normal infrastructure.