How do you intelligently surface access to your database? While at NDC Toronto, Richard spoke with Jerry Nixon about Data API Builder, Microsoft's tool that enables data professionals using Microsoft databases, including SQL Server, Postgres, CosmosDB, and MySQL, to provide an API layer with security, schema extraction, and governance policies. You can expose the API as a REST interface, a GraphQL interface, and an MCP server! This is a powerful tool for providing controlled access to data while...
Jun 03, 2026•37 min•Ep. 1039
How can Microsoft Loop make your team more productive? Richard chats with Karinne Bessette about the role that Loop components can play in making meetings where the agenda is live, generating work items in Microsoft Planner, and keeping key information up to date. Karinne talks about how Loop components can be connected to any M365 document, including Outlook, Word, Excel, and OneNote, but only for members of the M365 tenant. Loop is a powerful tool for productivity within the organization! Link...
May 27, 2026•36 min•Ep. 1038
The original Secure Boot certificate expires in June 2026! Richard talks to Richard Hicks about how Secure Boot works and how the expiration of the master certificate can leave PCs vulnerable to boot-related malware, such as rootkits. Richard discusses recent Microsoft communications on SecureBoot and how to check which certificate your machines have. Workstations using managed updates are likely already up to date, but servers are a different issue. When the certificate expires, you'll no longe...
May 20, 2026•38 min•Ep. 1037
What does a production-grade large language model look like? While at NDC Sydney, Richard talked with Vaishnavi Gudur from Microsoft about her work scaling LLMs for Teams transcriptions, summaries, and more! Vaishnavi discusses the underlying complexities of operating the Teams LLM infrastructure for a large array of customers across different countries and regulatory regimes. Data sovereignty also plays a large role: different countries have specific rules on where data must reside and how it c...
May 13, 2026•35 min•Ep. 1036
How secure is your Active Directory infrastructure? While at Zero Trust World in Orlando, Richard chatted with Spencer Alessi about his work helping companies secure Active Directory, making it more difficult for black hats to exploit it for lateral moves during a breach attempt. Spencer talks about the increasing speed of these exploits, making it much harder to block them after the fact, so it's best to make AD too difficult to target. Jake Hildreth's Locksmith tools are a great place to start...
May 06, 2026•37 min•Ep. 1035
There's competition in the Office productivity space! Richard chats with Sharon Weaver about her experiences with M365 Copilot and Anthropic's Claude Cowork to improve information worker productivity. Sharon talks about the confusion around all the different copilots in the Microsoft space - including the chat tools, research agents, and more. But when it comes to helping with an Excel spreadsheet, M365 Copilot can't do what Claude Cowork can do. Sharon talks about describing the goals of a spre...
Apr 29, 2026•39 min•Ep. 1034
What does the world look like after Microsoft Deployment Toolkit? Richard talks to MDT creator Michael Niehaus about the life and death of MDT. Michael talks about his early days at Microsoft, when he created a better way to manage operating system images so you can build and rebuild Windows PCs for your organization. But MDT had been in maintenance since 2013, without specific support for Windows 11. And now, some security concerns have ended support entirely. So what happens next? Michael offe...
Apr 22, 2026•39 min•Ep. 1033
How does your company communicate with its employees today? Richard chats with Emily Mancini about her work with companies that manage internal communications. Emily talks about the power of email, collaborative messaging like Teams, and the Microsoft Viva products Engage and Amplify. The conversation digs into knowing where your people look for info, how they communicate, and what they want to connect with. Being able to measure the response to different communication means helps you to work on...
Apr 15, 2026•35 min•Ep. 1032
AI Agents can be powerful tools for an organization - but are they a security risk? Richard talks to Niall Merrigan about his experiences dealing with the various ways that LLMs can be attacked, starting with prompt injection. While some attacks are humorous, others can be very serious, especially in the context of agents, where the right prompt can cause an agent to use its capabilities to access or affect data outside its expected behavior. This has already led to several well-publicized CVEs,...
Apr 08, 2026•38 min•Ep. 1031
Are you ready to take a look at Richard's home lab? Richard goes solo to share insights about the new infrastructure, hardware, and automation in his seaside home. He discusses the challenges posed by its remote location, including unreliable power and connectivity. You'll find plenty of details about networking, computing infrastructure, automation, telemetry, and experiments with AI technologies. Get an exclusive behind-the-scenes look! Links Kubernetes Ubiquiti Enterprise Campus Aggregation P...
Apr 01, 2026•10 min•Ep. 1030
Configuration drift is real - how do you control it in your Azure tenant? Richard talks to Nik Charlebois-Laprade about his ongoing work on desired state configuration DSC for Microsoft 365 tenants. Microsoft365DSC has been an open-source tool for managing configuration for some time, but today it has become a preview product called Unified Tenant Configuration in Microsoft Graph. Nik talks about managing multiple tenants, including a single tenant, using reference configurations that help you d...
Mar 25, 2026•34 min•Ep. 1029
How does artificial intelligence become more sustainable? Richard chats with Darshna Shah about her experiences as Chief AI Officer at Elastic. Darshna discusses the resources required to run large language model experiments, the pressure this has put on the electrical grid, and more. The conversation turns to efficiency - and the idea that there is little incentive in the current land grab around LLMs to be more efficient - that the focus is on growing quickly. But as technologies mature, effic...
Mar 18, 2026•43 min•Ep. 1028
SQL Server 2025 is released - what's in it, and what happens next? Richard chats with Bob Ward about the huge array of announcements coming out of Ignite around SQL Server 2025, including AI-related features, new reliability and performance options, engine improvements, and more! The tooling for SQL Server also continues to evolve, including making Copilot available through SSMS and as part of the SQL extension to Visual Studio Code. And there's more to come - have a listen! Links SQL Server 202...
Mar 11, 2026•40 min•Ep. 1027
How can you hire and get hired in 2026? While at NDC London, Richard chatted with Suzi Edwards-Alexander about her experiences recruiting technology folks into companies. Suzi talks about developing interview practices that actually reflect the job, rather than examining esoteric knowledge or certifications - it's possible to have an interviewing experience that is actually enjoyable! The conversation dives into the power imbalance between employers and employees and how to resist being seen as ...
Mar 04, 2026•49 min•Ep. 1026
What does it take to get your SaaS offering on multiple cloud providers? Richard chats with Steve Buchanan about his new role at JAMF, which focuses on a mobile device management product for Apple devices. Originally built as a SaaS product on AWS, Steve is helping to build out the JAMF stack on Azure to support a broader range of customers. Steve talks about Kubernetes as the common ground among the major cloud players, but you need to dig into the rest of the tooling to minimize differences ac...
Feb 25, 2026•39 min•Ep. 1025
How have large language models impacted hacking? Richard talks to Erica Burgess about her experiences using LLMs for red team hacking, collecting bug bounties, and identifying vulnerabilities in systems. Erica discusses the power of LLMs to generate a variety of viewpoints on a potential exploit and help the hacker think "out of the box." Coordinating multiple agents to attempt a variety of exploits, retrieve information, and otherwise deal with the drudgery parts of hacking means a skilled oper...
Feb 18, 2026•48 min•Ep. 1024
You're using Active Directory Certificate Services - but is it configured securely? Richard talks to Ron Arestia about his work with organizations implementing their own Public Key Infrastructure (PKI) with ADCS. Ron explains how poorly configured ADCS enables lateral attacks within an organization once an initial breach occurs, allowing black hats to move throughout your network. A well-designed PKI system has tiers of protection, with the top level completely disconnected from the network. Or ...
Feb 11, 2026•44 min•Ep. 1023
Ready to get started with Purview? Richard chats with Erica Toelle about the first steps you can take to harness the power of Purview in your organization. Erica explains that Purview is an umbrella product that covers several infosec technologies, including information rights management, data loss prevention, structured data governance, and more. When preparing for M365 Copilot, you want to start tagging sensitive information in your organization, and Purview can help by using LLMs to identify ...
Feb 04, 2026•31 min•Ep. 1022
Business Process Automation has been around a long time - what are the latest approaches? Richard talks to Ian Cooper about his work building BPA workflows in organizations - starting on paper or a whiteboard to make sense of the process before bringing tools into the equation. Ian talks about building repeatable workflows that are well-documented and source-controlled, typically through GitHub. As workflows get more complex, you'll need orchestration engines that can handle failures and provide...
Jan 28, 2026•38 min•Ep. 1021
How do you get an idea to implementation in your organization? Richard chats with Amber Vanderburg about the work she's done helping teams understand the process of getting projects started and finished. Amber talks about defining a clear starting line, ending line, and dead line. While many projects are important, prioritization is the challenge. This means often other priorities have to be resolved before something new can be started - you need resources and time to be successful. Working thro...
Jan 21, 2026•36 min•Ep. 1020
What's coming in 2026 for Azure? Richard chats with CVP and Chief Product Officer for Azure, Jeremy Winter, about the announcements at Ignite and what we can expect in Azure over the next year. Jeremy talks about new features for migrating workloads to Azure, creating more reliable application implementations, the vast array of AI-related technologies being released, and more! The conversation also digs into the new data centers being built all over the world, and how they are becoming more effi...
Jan 14, 2026•37 min•Ep. 1019
AI tools continue to evolve - what can we do with them today? Richard chats with Cecilia Wirén about her experiences using the latest AI tools to support DevOps workflows, diagnostics, and the crafting of new scripts. Cecilia focuses on tools that can help admins who occasionally work on scripts, including getting into a GitHub workflow to track prompts and results generated by LLMs, so you can always revert and learn from various approaches to interact with these new tools. The tools continue t...
Jan 07, 2026•41 min•Ep. 1018
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 ...
Dec 31, 2025•30 min•Ep. 1017
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. Wi...
Dec 24, 2025•43 min•Ep. 1016
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 elemen...
Dec 17, 2025•41 min•Ep. 1015
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 a...
Dec 10, 2025•41 min•Ep. 1014
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 conv...
Dec 03, 2025•41 min•Ep. 1013
The seasonal gift show is back - Joey Snow and Rick Claus bring their lists of great gifts for sysadmins. You know they're impossible to buy for, so we are making it easier for you with a range of prices and seriousness for your favorite sysadmin. Useful gadgets, upgrades to older devices, and some fun stuff that reminds the sysadmins in your life that you get their struggles. Share this show and toy list with everyone you know who struggles to find the right thing! Links USB Tester Battery Dadd...
Nov 26, 2025•37 min•Ep. 1012
How can Azure Site Reliability Engineering Agents help your Azure infrastructure? While at Techorama in Utrecht, Richard chatted with Deepthi Chelupati about the LLM service that helps you build and maintain more reliable applications and infrastructure in Azure. Deepthi talks about monitoring deployment problems, handling errors in production, and application telemetry in operation as areas where Azure SRE Agents can help catch issues earlier and let you respond faster. The conversation dives i...
Nov 19, 2025•34 min•Ep. 1011
How resilient are your Azure deployments? Richard chats with Chris Ayers about his work on Azure reliability - not only for customers using Azure, but for Azure itself! Chris focuses on the Well-Architected Framework as a guideline for thinking through all the elements of resiliency in Azure. As with all things, there are trade-offs of cost and reliability - you'll want to build a spreadsheet to balance the cost of an outage against the expenses of resiliency services in Azure - and your own lab...
Nov 12, 2025•39 min•Ep. 1010
