
The SysAdmin in 2026
2025-12-31 | 29 mins.
A new year - and so much to do! To start 2026, Richard flies solo again to discuss the issues he's seen on sysadmins' minds as we head into the new year. Obviously, AI is eating up a lot of the conversation from many different angles: tools that can help us be more productive, security issues in our organizations due to misuse, and now, AI-driven hacking. Security still looms large, and not just from an AI perspective - the latest round of supply chain attacks has led to litigation, putting new emphasis on making sure you're secure. Windows has a new leader, things are changing there, and there's the ongoing migration to the cloud. Does it still make sense? There seems to be more concern about data sovereignty than ever, and some meaningful conversations to have. Happy New Year!LinksAzure SRE Agents with Deepthi ChelupatiMicrosoft PurviewThe M365 Copilot Data Readiness Checklist with Nikki ChappleQuering for Breaches with Mark MorowcyznskiManaging Vendor Incidents with Mandi WallsIncident Management and the Crowdstrike event with Lieam WestleyMicrosoft IntuneMicrosoft Entra IDMicrosoft Defender for EndpointMicrosoft Entra ID Protection with Corissa KoopmansWindows Server 2025Upgrading to Windows Server 2025 with Robert SmitRecorded December 20, 2025

What Windows Wants for Christmas with Paul Thurrott
2025-12-24 | 42 mins.
So what does Windows want for Christmas? Paul Thurrott is back to talk about everything that happened to Windows in 2025, and what that might hold for 2026. Paul talks about Pavan Davuluri being promoted to President of Windows & Devices - and reunifying the Windows Client and Windows Core teams. That sets up an opportunity to make some significant moves from Windows, which, of course, will involve AI - although the reaction to the public when Pavan said as much was not all that positive. Windows has plenty of problems to address, but one of the brighter notes is Windows on ARM and the Snapdragon processor. And maybe, just maybe, someone's wish will come true, and we'll see Windows 12!LinksPavan's Famous AI TweetM365 CopilotMicrosoft LoopMicrosoft RecallRecorded December 16, 2025

Zero Trust in 2026 with Michele Bustamante
2025-12-17 | 41 mins.
How is zero-trust security evolving? Michele Leroux Bustamante discusses the challenges CISOs face today in controlling access to infrastructure, authenticating and authorizing users, and managing the ongoing evolution of an organization's dependencies. The conversation digs into the variety of stacks available to address various elements of an organization's security requirements. Michele also talks about the NIST Cybersecurity Framework as a starting point for understanding the security elements your organization needs to focus on and improve—security is a continuum, not a destination!LinksAzure EntraAuth0DuendeKeyCloakNIST Cybersecurity FrameworkOpen Policy AgentPolicy ServerDefender for CloudAzure API ManagementAzure Front DoorRecorded October 29, 2025

Incident Management and the Crowdstrike Event with Liam Westley
2025-12-10 | 41 mins.
On July 19, 2024, a misconfigured file sent as part of an update to the Falcon Sensor suite by CrowdStrike caused service outages worldwide. Liam Westley talks about his experiences executing the incident management plan at his company that day—even though his company did not use the software! Liam talks about dealing with the regulatory requirements of a finance company as part of incident planning, and how the software and services supply chain can lead to outages because those companies are affected. A great story about the day of the incident and the improvements in planning and resiliency that followed!LinksCrowdStrike Incident TimelineAzure Front DoorRecorded October 29, 2025

The M365 Copilot Data Readiness Checklist with Nikki Chapple
2025-12-03 | 40 mins.
What does it take to be ready to deploy M365 Copilot in your organization? Richard talks to Nikki Chapple about her latest incarnation of the M365 Copilot Readiness Checklist, working step-by-step to bring M365 Copilot into the organization without causing data leak issues. Nikki discusses utilizing existing tools to accurately identify sensitive data, archiving outdated information, and monitoring data usage by both users and agents - allowing you to detect issues before they escalate. The conversation also delves into the process of identifying issues, discussing policy changes, and how to communicate those changes so that people can take advantage of the power of these new tools without feeling threatened. It's a journey!LinksMicrosoft PurviewSharePoint Advanced ManagementDefender for Cloud AppsRestricted SharePoint SearchMicrosoft 365 ArchiveSharePoint Restricted Content DiscoveryData Security Posture Management for AINikki's Readiness ChecklistM365 Copilot Oversharing BlueprintMicrosoft Purview Secure by Default BlueprintPrevent Data Leaks to Shadow AI BlueprintRecorded November 7, 2025



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