Microsoft Cloud IT Pro Podcast

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.

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

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!

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.

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

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!

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.

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

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!

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.

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

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!

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.

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)

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!

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.

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.

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.

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

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

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!

Welcome to Episode 424 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben and Scott dig into the newly announced Microsoft 365 E7 SKU which bundles M365 E5, Microsoft 365 Copilot, the Microsoft Entra Suite, and Microsoft Agent 365.

Partner Blog | Introducing Microsoft 365 E7: The Frontier Suite

Powering Frontier Transformation with Copilot and agents

Microsoft Entra Suite

Microsoft Entra Suite deployment scenarios introduction

Microsoft Agent 365

Overview of Microsoft Agent 365

Use Microsoft Intune Suite add-on capabilities

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

Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

Welcome to Episode 423 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben is live from Workplace Ninjas, joined by Eric Woodruff, Chief Identity Architect at Semperis and Microsoft MVP in Security focused on identity, and Chris Brumm, Cyber Security Architect at glueckkanja and Microsoft MVP in Security with over 16 years of experience in cybersecurity. Together they dig into the often-overlooked world of non-human identities in Microsoft Entra ID. They cover what service principals are, why they tend to fly under the radar compared to user accounts, and how attackers actively exploit that gap. The conversation spans credential management best practices, the risks of improper owner assignments, the challenges of multi-tenant app configurations, and why managed identities should be your go-to wherever possible. They also discuss the growing challenge of AI agent identities and what IT pros need to start thinking about now before that surface area explodes.

Eric Woodruff on LinkedIn

Eric Woodruff on X (@ericanidentity)

Eric on Identity

Chris Brum on LinkedIn

Chris Brumm on X (@cbrhh)

Chris Brumm’s Blog

Application and service principal objects in Microsoft Entra ID

Workload Identities

Securing service principals in Microsoft Entra ID

Securing managed identities in Microsoft Entra ID

Conditional Access for Workload Identities

Microsoft Entra Audit Logs

Microsoft Sentinel Detection Templates

Eric Woodruff

Eric Woodruff is the Chief Identity Architect at Semperis and a Microsoft MVP in Security with a focus on identity. He specializes in all things Microsoft Entra and Active Directory, with a passion for helping organizations understand and secure both human and non-human identities. You can find Eric on social media as @ericanidentity.

Chris Brumm is a Cyber Security Architect at glueckkanja based in Germany, with over 16 years of experience across virtually every corner of cybersecurity. He is a Microsoft MVP in Security with a primary focus on identity security. His team operates SOC services and he brings a detection and response perspective to identity risk, helping organizations build lifecycle processes and monitoring strategies for non-human identities in Microsoft Entra.

M365 Licensing Consultation

M365 Tenant Assessment

Copilot Readiness Assessment

Welcome to Episode 422 of the Microsoft Cloud IT Pro Podcast. In this episode, Scott and Ben discuss their growing use of   in their daily workflows, particularly Claude Code, GitHub Copilot CLI, and Gemini CLI. They explore how these command-line interfaces offer powerful ways to interact with local files and MCP servers beyond traditional desktop AI chat interfaces. They share how they are using these tools in their day-to-day roles to perform different tasks and accelerate their workflows.

Claude Code overview

Using Claude in PowerPoint

Create custom subagents

Microsoft Work IQ CLI (Public Preview)

https://github.com/obra/superpowers

How to Use Claude Code: A Guide to Slash Commands, Agents, Skills, and Plug-ins

Gemimi CLI overview

Github Copilot overview

Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

Welcome to Episode 421 of the Microsoft Cloud IT Pro Podcast. In this episode Ben sits down for a conversation with Frank Lesniak, the lead of the Microsoft 365 team at West Monroe. In this episode, they dive into the intricacies of mergers and divestitures within Microsoft 365 environments. They discuss the initial due diligence phase, planning and approach, building and configuring new environments, and the final migration and cutover phase. Frank shares insights on common challenges such as integration of different licensing models, the handling of workstations and applications, and the importance of security assessments. The episode provides a detailed look at the methodology and tools used by Frank’s team to streamline these complex processes.

Frank Lesniak on LinkedIn

West Monroe

Frank Lesniak Github

Microsoft 365 tenant-to-tenant migrations

Microsoft 365 inter-tenant collaboration

Tenant life cycle considerations in multitenant solutions

Frank Lesniak is a Sr. Cybersecurity & Enterprise Technology Architect at West Monroe with nearly 20 years of experience leading consulting engagements involving Microsoft infrastructure technology. His expertise spans modern cloud systems like Azure, Microsoft 365, and Entra ID to classic platforms like Windows Server, Active Directory, and SQL Server. His recent focus has been on Microsoft platform cybersecurity and automating technical processes using PowerShell. In his role, Frank establishes technical project methodologies, leads teams, automates associated processes, and creates internal software products at West Monroe and in the open-source community.

Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!