Modern IT environments are held together by a patchwork of legacy infrastructure, half-finished cloud migrations, misconfigured identity systems, and architectural “temporary fixes” that somehow became permanent. In this super-session, Dave walks through the 12 most catastrophic infrastructure failures he encounters in real customer environments — from Active Directory fragility to broken DNS, hybrid identity chaos, unscalable Azure VNets, misconfigured storage, orphaned VMware clusters, corrupted GPO inheritance, outdated hypervisors, insecure backup architectures, and more.

This is not a theoretical talk. These are the exact problems causing outages, service degradation, failed migrations, authentication delays, Teams instability, Azure AD sync failures, random VMs rebooting, cluster split-brain, backup timeouts, and crippling ransomware blast radius in real environments right now.

Attendees will walk away with a full roadmap to modernize their entire environment, whether hybrid or on-prem, using practical, field-tested fixes, ASCII diagrams, modernization sequences, migration paths, and checklists drawn directly from Dave's largest enterprise projects in 2025–2026.

This is the talk that saves people’s weekends.

1. Broken DNS That Nobody Knows Is Broken

Split-brain messes, bad resolvers, wrong forwarders, invisible caches, and the #1 cause of all cloud failures.

2. Active Directory Rot & Technical Debt (2003–2025)

Lingering objects, stale DCs, outdated SYSVOL, inconsistent sites/subnets, lingering legacy encryption.

3. Hybrid Identity Time Bombs (AADC, Entra, SSO)

Improper UPNs, bad attribute flows, sync loops, dual-password worlds, CA misalignment.

4. Flat Networks With No Segmentation

The opposite of Zero Trust — printers, domain controllers, HVAC, and servers all partying together.

5. Outdated Hypervisors Running Mission-Critical Workloads

Clusters never patched, 20-second VM pauses, orphaned datastores, no hardware isolation.

6. Storage Architectures Built for 2010 Workloads

Old SAN firmware, dead cache batteries, S2D misconfiguration, iWarp disaster stories.

7. Broken Azure Networking (The #1 Problem in Cloud Deployments)

Misaligned address spaces, busted hub/spoke, overlapping ranges, ER routing blackholes.

8. Disaster Recovery Plans That Don’t Work in Reality

Unbootable backups, missing AD, broken trust, Veeam misconfiguration, no clean room.

9. Group Policy Chaos & Years of Inheritance Rot

10 layers of conflicting GPOs, loopback disasters, orphaned settings, slow login storms.

10. Endpoint Management Split-Brain (GPO + Intune Fighting Each Other)

Security baselines battling legacy GPO settings → compliance drift → broken devices.

11. Monitoring & Logging That Shows You Everything Except What You Need

Siloed dashboards, too many agents, no correlated view, no insight into real root cause.

12. No Patch Management Strategy Across Hybrid Servers

Azure Arc not deployed → on-prem servers unmanaged → patch drift → CVE exposure.