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 operator can move faster - what once would be days of work can be minutes. Where does AI in hacking go? Lots of scary places - but also pointing the way to new ways to protect systems!

Links

• Burninator Sec

Recorded January 24, 2026

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 do you really need your own PKI system? The conversation digs into the various scenarios, including third-party options. Certificates are the top level of security for your organization - you need to get it right!

Links

• Active Directory Certificate Services
• Windows Hello for Business
• Certified Pre-Owned
• Microsoft Defender for Identity
• Secure Privileged Access
• Pass the Hash
• Microsoft Cloud PKI for Microsoft Intune
• Microsoft Entra Conditional Access
• Microsoft Autopilot
• Ron's Blog

Recorded February 6, 2026

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 potentially sensitive content. You can also monitor how data is used, the types of prompts sent to M365 Copilot, and more. This can help you bootstrap M365 Copilot by using Purview to see which data Copilot uses, and then tune the access rules for that data. "Getting your data estate in order" is not a destination; it's a journey, and Purview can give you a map!

Links

• Microsoft Purview
• Data Security Posture Management
• Data Governance with Microsoft Purview
• Conditional Access with Microsoft Purview
• SharePoint Advanced Management
• Microsoft 365 Archive
• Endpoint Data Loss Prevention
• Purview Browser Extension

Recorded January 7, 2026

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 telemetry to identify when and where things go wrong. And make sure you let users know how things are going - or they will worry!

Links

• Kafka
• Durable Functions
• GitHub Actions
• Temporal
• Pulumi
• OpenTelemetry

Recorded December 5, 2025

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 through the process takes time, but the alternative is failure to meet expectations. It takes planning and clear communication to get things done!

Links

• Pathwayz Group
• Mythical Man Month
• The Four Disciplines of Execution
• Speed of Trust
• The Culture Map

Recorded December 4, 2025

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 efficient with resources.

Links

• Azure Copilot
• Azure SRE Agent
• Azure Resiliency Agent
• Azure Migrate
• Kubernetes Fleet
• Azure HorizonDB
• Azure Red Hat OpenShift
• Azure Fairwater

Recorded December 3, 2025

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 to evolve; it's worth looking at the latest features and models!

Links

• Azure SRE Agent
• Microsoft Security Copilot
• GitHub Copilot
• Awesome Copilot
• Copilot Extensions

Recorded December 3, 2025

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!

Links

• Azure SRE Agents with Deepthi Chelupati
• Microsoft Purview
• The M365 Copilot Data Readiness Checklist with Nikki Chapple
• Quering for Breaches with Mark Morowcyznski
• Managing Vendor Incidents with Mandi Walls
• Incident Management and the Crowdstrike event with Lieam Westley
• Microsoft Intune
• Microsoft Entra ID
• Microsoft Defender for Endpoint
• Microsoft Entra ID Protection with Corissa Koopmans
• Windows Server 2025
• Upgrading to Windows Server 2025 with Robert Smit

Recorded December 20, 2025