Microsoft Cloud IT Pro Podcast

Hosted by Ben Stegink, Scott Hoag

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Jul 2026

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About the show

Your Microsoft Cloud News from a couple of IT Pros

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60 recent

August 13, 202647 min

Episode 434: Reading the Spec Sheet on Microsoft’s Agentic SOC

Welcome to Episode 434 of the Microsoft Cloud IT Pro Podcast. Microsoft announced Project Perception on 2026-07-27 with a lot of “workforce of AI agents” language. In this episode, Ben and Scott discuss what Perception really is, what it needs from your tenant, what it costs, and what happens the first time an agent asks you to approve something. Six agents. Seven playbooks. Every one manually triggered. Each agent gets its own Entra Agent ID and a permission grant. There’s a lot to unpack. Your support makes this show possible! Please consider becoming a premium member for access to live shows and more. Check out our membership options. Show Notes Save $200 at TechCon365 with code Ben200: https://www.techcon365.com/Seattle/ What is Project Perception? How Nationwide stays ahead of attackers with Project Perception Key concepts in Project Perception Agent categories in Project Perception Microsoft Security Copilot Security Compute Units and capacity Work with playbooks in Project Perception Prior podcast context Ep 431: Agent Governance Is the New App Governance Ep 419: Security and AI Ep 416 and Ep 412 Ep 406: Agents of Insight Ep 377: Microsoft Copilot for Security Sponsors Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. Nasuni powers the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits. Intelligink — Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

July 30, 202645 min

Episode 433: Passkeys, Passwords, and the End of SMS MFA

Welcome to Episode 433 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben and Scott discuss how Microsoft 365 authentication is moving from “make passwords safer with MFA” to “remove phishable authentication wherever possible.” The practical conversation for IT pros is no longer just whether MFA is enabled. It is which methods are allowed, which users are still on SMS or voice, how passkeys change the user experience, and how to balance security, accessibility, recovery, and support load. Your support makes this show possible! Please consider becoming a premium member for access to live shows and more. Check out our membership options. Show Notes Passkeys were supposed to replace passwords, but they’re failing for the most predictable reason Microsoft Entra authentication overview Passkeys by default and retirement of Microsoft-provided SMS and voice authentication Plan a phishing-resistant passwordless authentication deployment in Microsoft Entra ID Run a registration campaign to set up a passkey or Microsoft Authenticator Practical Protection: Understanding Entra ID and Passkeys Important Change Coming for Entra ID Passkeys in November 2025 Microsoft to Stop Providing Telephony-Based Authentication Methods for MFA in February 2027 How to enable passkeys (FIDO2) in Microsoft Entra ID Sponsors Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. Nasuni powers the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits. Intelligink — Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

July 16, 202642 min

Episode 432: AI-Era Consulting Billing for Microsoft Cloud Delivery

Welcome to Episode 432 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben and Scott discuss how AI is not eliminating Microsoft 365 and Azure consulting, but it is changing what clients think they are buying. Your support makes this show possible! Please consider becoming a premium member for access to live shows and more. Check out our membership options. Show Notes Inside Consultants’ Messy Shift From Hourly Billing Episode 431: Agent Governance Is the New App Governance Microsoft 365 Copilot readiness report Microsoft 365 Copilot usage report Microsoft Secure Score Sponsors Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. Nasuni powers the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits. Intelligink — Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

July 2, 202648 min

Episode 431: Agent Governance Is the New App Governance

Welcome to Episode 431 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben and Scott get into why agent governance is quickly becoming one of the most pressing challenges for Microsoft 365 administrators. As agentic workflows become more common across Copilot, Copilot Studio, and third-party platforms, organizations are dealing with a sprawl problem that looks familiar but hits differently. Agents bring their own identity, data access, permissions, lifecycle, and security concerns all at once, and unlike traditional apps, a single user can now have dozens of agents acting on their behalf or autonomously across Teams, SharePoint, Exchange, and beyond. The episode walks through Microsoft Agent 365 as a starting point for building that control plane, including the agent registry, user and permission scoping, and the certification tab where publisher attestation gives some visibility into compliance claims though with notable gaps. Ben and Scott also touch on the Shadow AI preview in the Frontier program, the challenges of graph permission readability in the permissions view, and why the agent lifecycle problem, think what happens when the person who built a custom agent leaves the org, is something administrators need to start thinking about now before consumption billing turns an unmanaged agent into a surprise line item. Your support makes this show possible! Please consider becoming a premium member for access to live shows and more. Check out our membership options. Show Notes Overview of Microsoft Agent 365 Episode 409 – Preparing for Copilot- Securing Your Microsoft 365 Data and Beyond Episode 425 – Exploring Collaboration and Governance at the MVP Summit with Joy Apple Manage agents in the Microsoft 365 admin center Agent management in Microsoft 365 admin center Shadow AI in Microsoft 365 admin center (Preview) Understand agent details in Microsoft 365 admin center Sponsors   Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. Nasuni powers the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits. TrustedTech is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Their robust team of in-house, U.S.-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program. M365 Licensing Consultation M365 Tenant Assessment Copilot Readiness Assessment ShareGate is your migration and governance solution for Microsoft 365. ShareGate helps your teams simplify tenant migrations, get Copilot-ready, and take control of Microsoft 365 governance. Intelligink — Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

June 18, 202643 min

Episode 430: Scouting out Microsoft Scout

Welcome to Episode 430 of the Microsoft Cloud IT Pro Podcast, where Scott and Ben dig into Microsoft Scout, the new desktop AI application announced at Microsoft Build. They walk through the real onboarding experience on both Mac and Windows, the licensing maze and admin controls needed to activate it, and how Scout’s architecture ties together models, automations, and integrations like MCP, GitHub Copilot, and Work IQ. Along the way they cover the model selector and personality options (everything from professional to sarcastic teenager), the automations and heartbeats that run on schedules to update you on industry news, monitor workflows, and manage meetings, and the limitations and workarounds around skills, session management, and local file access. They also sort out where Scout overlaps with and differs from Microsoft 365 Copilot and GitHub Copilot, how to rationalize all three for ROI, and what token-based, consumption-based pricing means for enterprise AI strategy. Whether you’re a pilot user or just AI-curious, this episode cuts through the hype to show why Scout’s local-first approach is a game-changer for MCP workflows, custom skills, and offline automation, and what it actually takes to adopt Scout as your desktop AI hub. Hosted by Scott and Ben, two industry veterans passionate about AI and automation, it delivers practical, actionable insights for technical leaders, developers, and productivity enthusiasts. Join us as we unravel Scout’s potential to redefine your desktop AI experience, because knowing how to navigate its complexities now can save you time and money tomorrow. Show Notes Introducing Microsoft Scout: Your always-on personal agent Microsoft Scout (Frontier) documentation Announcing the new Work IQ APIs Work IQ: Production‑ready intelligence for every agent Get started with Microsoft Scout Admin access overview for Microsoft Scout Microsoft Scout — Automations, Memory, Heartbeats Sponsors TrustedTech is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Their robust team of in-house, U.S.-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program. M365 Licensing Consultation M365 Tenant Assessment Copilot Readiness Assessment ShareGate is your migration and governance solution for Microsoft 365. ShareGate helps your teams simplify tenant migrations, get Copilot-ready, and take control of Microsoft 365 governance. Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. Nasuni powers the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits. Intelligink — Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

June 4, 202644 min

Episode 429: Getting started with LLM Wikis

Welcome to Episode 429 of the Microsoft Cloud IT Pro Podcast. In this episode, Scott and Ben dig into the concept of LLM wikis, specifically building personal knowledge management vaults using Obsidian, markdown, and AI tooling like Claude Code, GitHub Copilot CLI, and Copilot Cowork. The core idea comes from a gist by Andrej Karpathy and involves creating a structured folder of markdown clippings that an LLM can reason over to extract entities, concepts, and sources, building a searchable, graph-linked knowledge base over time. Scott walks through how he wired up Obsidian Web Clipper and an RSS Dashboard plugin to feed articles into his vault automatically, then had the LLM help build a Python script to automate the ingest workflow and cut down on token usage. The conversation expands into how Copilot Cowork fits into this workflow as a scheduling harness, with practical examples of using it to pull email from an inbox daily, convert messages to markdown, and generate a prioritized to-do list. Ben shares how he applied the same approach to 428 episodes of podcast transcripts, and both hosts note that token costs can run high fast without some upfront thinking about optimization. Scott closes with a reminder that pulling data into plain markdown sidecars outside of IRM and sensitivity label protections means teams should stay mindful of organizational data policies. Your support makes this show possible! Please consider becoming a premium member for access to live shows and more. Check out our membership options. Show Notes LLM Wiki GitHub Copilot Wiki: An AI-Powered Second Brain Template Karpathy’s LLM Knowledge Base Wiki for Enterprise Karpathy’s LLM Wiki? No Code with Claude or Github Copilot! sametbrr/llm-wiki-manager Sponsors TrustedTech is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Their robust team of in-house, U.S.-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program. M365 Licensing Consultation M365 Tenant Assessment Copilot Readiness Assessment ShareGate is your migration and governance solution for Microsoft 365. ShareGate helps your teams simplify tenant migrations, get Copilot-ready, and take control of Microsoft 365 governance. Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. Nasuni powers the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits. Intelligink — Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

May 21, 202641 min

Episode 428: Migrating Group Policy to Microsoft Intune

Welcome to Episode 428 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben and Scott unlock the secrets to modernizing your IT management by ditching pesky on-prem GPOs and embracing the future with Intune. They discuss how savvy IT pros are migrating thousands of GPOs into clean, manageable cloud policies. Dive into real-world workflows: from exporting and analyzing legacy GPOs with AI tools, to recreating policies in Entra ID, and finally decommissioning AD. You’ll discover how to think through the migration, avoid common pitfalls like leftover legacy configs, and implement a phased migration that minimizes disruption. Your support makes this show possible! Please consider becoming a premium member for access to live shows and more. Check out our membership options. Show Notes DiskPrices.com These HDD prices are getting crazy. An increase of 96.4% in 1 month for the same 26TB drive. $279.99 a month ago to $549.99 today. Where are we buying hard drives now? Import and analyze your on-premises GPOs using Group Policy analytics in Microsoft Intune Microsoft Copilot in Intune Policy CSP Use the Intune settings catalog to configure settings Use the Intune properties catalog to get device hardware properties Create a Settings Catalog policy using your imported GPOs in Microsoft Intune Sponsors   ShareGate is your migration and governance solution for Microsoft 365. ShareGate helps your teams simplify tenant migrations, get Copilot-ready, and take control of Microsoft 365 governance. Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. Nasuni powers the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits. TrustedTech is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Their robust team of in-house, U.S.-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program. M365 Licensing Consultation M365 Tenant Assessment Copilot Readiness Assessment Intelligink — Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

May 7, 202632 min

Episode 427: Copilot Cowork Hands-On Experiences

Welcome to Episode 427 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben and Scott open with a quick look at YAKO (getyako.com), a browser extension built by community member Merrill that replaces the new tab page with a customizable dashboard of Microsoft 365 and cloud links. From there, the conversation turns into an extended follow-up on Copilot Cowork, covering some of their recent hands-on experience with custom skills, artifact management, session crashes tied to an Anthropic API outage, and the friction of working with IRM-protected documents in Copilot Cowork. The bigger thread running through the episode is data security. Listen in to hear more about considerations for onboarding to Copilot Cowork in its early days. Your support makes this show possible! Please consider becoming a premium member for access to live shows and more. Check out our membership options. Show Notes Yako Get started with Cowork (Frontier) How does Cowork handle my data? Does Cowork connect to external models for processing? Are there unsupported countries/regions? Sensitivity labels for Microsoft 365 Copilot and Microsoft 365 Copilot Chat Sponsors TrustedTech Team is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Their robust team of in-house, U.S.-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program. M365 Licensing Consultation M365 Tenant Assessment Copilot Readiness Assessment ShareGate is your migration and governance solution for Microsoft 365. ShareGate helps your teams simplify tenant migrations, get Copilot-ready, and take control of Microsoft 365 governance. Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. Nasuni powers the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits. Intelligink — Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

April 23, 202651 min

Episode 426: Claude Cowork vs Microsoft 365 Copilot Cowork

Welcome to Episode 426 of the Microsoft Cloud IT Pro Podcast.Ben and Scott are back together this week to talk through Microsoft 365 Copilot Cowork, including how it compares to Claude Cowork and where each one makes sense. The two products share a name but work pretty differently. Claude Cowork runs locally on your desktop and can access files on your machine, supports MCP server connections while M365 Copilot Cowork runs in the cloud, requires files to be in OneDrive, and does not support MCP connectors yet. On the flip side, the Microsoft version runs scheduled tasks without needing your machine to be on, has native access to all your M365 data through Graph, and fits inside your existing compliance and security controls through Purview, which matters a lot for regulated organizations. Your support makes this show possible! Please consider becoming a premium member for access to live shows and more. Check out our membership options. Show Notes Quentin Amaudry – As everyone knows, Cowork is coming within Copilot and it is extremely promising Copilot Cowork vs Claude Cowork: Same AI, Different Worlds Copilot Cowork: A new way of getting work done Cowork overview (Frontier) About the sponsors   TrustedTech is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Our robust team of in-house, U.S-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program. M365 Licensing Consultation M365 Tenant Assessment Copilot Readiness Assessment Your migration and governance solution for Microsoft 365. ShareGate helps your teams simplify tenant migrations, get Copilot-ready, and take control of Microsoft 365 governance. Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. We power the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits. Visit nasuni.com to learn more. Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

April 9, 202650 min

Episode 425 – Exploring Collaboration and Governance at the MVP Summit with Joy Apple

Welcome to Episode 425 of the Microsoft Cloud IT Pro Podcast. In this audio and video episode recorded live at Microsoft headquarters during the MVP Summit, Ben welcomes a return guest, Joy Apple, to the Microsoft Cloud IT Pro Podcast and discuss her 20-year career in the Microsoft collaboration space, from financial services to SharePoint training, consulting, and her current role at Orchestry Software. Joy explains Orchestry as a Microsoft 365 governance automation layer covering templated provisioning for SharePoint and Teams, archiving policies (including Microsoft 365 Archive), guest management, and OneDrive governance. They emphasize that AI and Copilot amplify existing information architecture, permissions, and data hygiene issues, making governance more critical. They describe the MVP Summit as a “family reunion” where MVPs attend sessions and reconnect with peers. Joy and Ben also spend some time describing paths becoming an MVP and how much they just enjoy the community around the Microsoft 365 ecosystem and connecting with people both at MVP Summit as well as various conferences throughout the year. About Joy Apple Joy is a Microsoft MVP and Director of Success and Enablement at Orchestry. With years of experience as an information technologist, I’m dedicated to helping organizations implement technology with a purpose-driven, “human-first” approach, ensuring tools like Microsoft 365 empower people to do their best work. Teaching and knowledge-sharing are at the heart of what I do. Whether it’s through volunteering in the Microsoft Community, speaking at events, or writing as the “Joy of SharePoint,” I’m passionate about helping others unlock their potential with modern workplace solutions. Im also a cohost of the Guardians of M365 Governance podcast, where I explore the challenges and rewards of governance, and a columnist for She is Tulsa, a quarterly magazine celebrating impactful stories from my local community. Outside of work, you’ll often find me enjoying live music or discovering new spots in Tulsa, Oklahoma, combining my love of connection and creativity wherever I go. Show Notes See the recording from the Microsoft Studios! Joy Apple on LinkedIn The Microsoft 365 Maturity Model – Governance, Risk, and Compliance Competency The Microsoft MVP Communities About the MVP Program Overview of Microsoft 365 Archive Guests in the Microsoft 365 admin center Mitigate Oversharing to Govern Microsoft 365 Copilot and Agents Orchestry About the sponsors   TrustedTech is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Our robust team of in-house, U.S-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program. M365 Licensing Consultation M365 Tenant Assessment Copilot Readiness Assessment Your migration and governance solution for Microsoft 365 ShareGate helps your teams simplify tenant migrations, get Copilot-ready, and take control of Microsoft 365 governance. Our Microsoft 365 experts and Microsoft Azure experts focus on the Microsoft cloud, so you can focus on what you do best! Learn more how we can help you!