Microsoft is finally enforcing certificate-based authentication at the enterprise level with Windows 11, and it's about to break your legacy on-premises infrastructure. Lucas walks through the timeline: starting with the 24H2 update, devices joined to Azure AD or hybrid Azure AD will require certificate auto-enrollment via ADCS or a third-party PKI. Luna digs into the real-world pain: IT teams still using self-signed certs or manual enrollment for VPN, Wi-Fi, and email S/MIME will face failed connections. They cover the three biggest impact areas: network access, email encryption, and application authentication. Lucas shares a concrete example from a mid-size healthcare firm that discovered 40% of their laptops were still using password-based Wi-Fi profiles. The episode closes with a practical checklist: audit your PKI, validate your auto-enrollment GPO, and test with a Windows 11 pilot group. No alarmism here — just a clear map of what's coming and how to prepare before the 24H2 rollout hits your fleet.