In this episode, Andy teams up with Microsoft expert and Aussie tech legend Paul Schnackenburg to break down the buzzword that’s haunting every IT strategy deck: Cloud-Native. Together, they unpack what it really means in a Microsoft ecosystem from ditching on-prem Active Directory and ConfigMgr to embracing Entra ID, Intune, and Autopilot.

Along the way, they hit on real-world migrations, the trade-offs of control vs. convenience, and why hybrid identity might actually make you less secure. Expect analogies about Death Stars, cruise ships, and even the Magic School Bus, because of course they did.

Whether you’re an MSP plotting your clients’ next move or an IT pro trying to future-proof your environment, this episode’s your field guide to surviving (and thriving) in a Cloud-Native world.

NOTE: As a reminder, be sure to share your IT Horror stories with us! We’d love to share as many as we can during an upcoming Halloween episode!

Episode Resources:

- CVE-2025-32463 (Sudo vulnerability details)

- CISA KEV Catalog (Known Exploited Vulnerabilities)

- SysAdmin Weekly Episode 22 – IT Documentation (Referenced in comments segment)

- SysAdmin Weekly Episode 3 – WSUS Deprecation Discussion

- Azure Files Overview

- Microsoft Intune Autopilot Device Preparation (v2)

- Microsoft Universal Print

- Windows Autopatch Overview

- Azure Arc for Servers

- PowerShell Summit Session: Secure Management of Secrets with Azure Arc (Referenced by Andy)

- SysAdmin Weekly Companion Newsletter

- Contact the show