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!

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!

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!

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. 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 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 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 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. Show Notes 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 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.   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 At Intelligink, our focus is singular: the Microsoft cloud. Our Microsoft 365 and Azure experts help you work securely and efficiently by unlocking the full value of what you’re already paying for, so you can focus on running your business.

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

Welcome to Episode 420 of the Microsoft Cloud IT Pro Podcast. In this episode, Scott is back for a lighthearted discussion on some of the new tech and toys and that Ben and Scott picked up over the holidays. Listen in as Ben tries to convince Scott he needs a 3D printer and some feedback on the gadgets they both picked up. 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 Bambu Lab P2S 3D Printer ViewSonic VP2788-5K 27″ 5K Mac-Ready Monitor with 100% sRGB, 99% DCI-P3, Pantone Validated, Advanced Ergonomics, Thunderbolt 4, USB Hub, HDMI, and DP for Home and Office Everyone needs a UPS Logitech MX Master 4, Ergonomic Wireless Mouse with Advanced Performance Haptic Feedback, Ultra-Fast Scrolling, USB-C Charging, Bluetooth, Windows, MacOS Aqara Presence Sensor FP300 Wireless 5-in-1 Motion Sensor with mmWave, PIR, Light, Temperature & Humidity Detection, Thread & Zigbee, Supports HomeKit, Home Assistant, Alexa, Google Home Unifi Motion Sensor About the sponsors Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

Welcome to Episode 419 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben is once again live from Workplace Ninjas and is joined by John Joyner, an 18-year Microsoft MVP in Cloud Security and Azure Management. They discuss some of the announcements from Microsoft Ignite focused around Microsoft Security as well as diving deep into the new Security Store, AI agents, Security Compute Units (SCUs), and how Microsoft is making enterprise AI security more accessible and affordable than ever. Key topics include the phishing triage agent, conditional access optimization, E5 integration with included SCUs, and the strategic consolidation of security services into the Defender XDR portal. Whether you’re a security professional or IT administrator, this conversation provides valuable insights into Microsoft’s AI-driven security roadmap and how to stay ahead of AI-powered threats. 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 John Joyner on LinkedIn John Joyner’s Blog John Joyner’s Books Corica Technologies What is Microsoft Security Copilot? Security Store Microsoft Security Copilot agents overview Learn about Security Copilot inclusion in Microsoft 365 E5 subscription Microsoft Security Copilot Phishing Triage Agent in Microsoft Defender John Joyner John Joyner is an inventor, author, speaker, and professor specializing in datacenter and enterprise cloud computing. He serves as Senior Director of Technology at Corsica Technologies (formerly AccountabilIT), where he delivers next-generation technology management services to customers worldwide as a cloud architect helping businesses stay competitive. John is a Microsoft Azure MVP and Security MVP, having been recognized eighteen times (2007-2026) as a Microsoft Most Valuable Professional for his exceptional technical expertise, leadership, speaking experience, online influence, and commitment to solving real-world problems. He holds a Bachelor of Science in Business Administration with an Emphasis in Human Resources Management from the University of Colorado at Boulder. From 2007 to 2024, John served as an Adjunct Professor at the University of Arkansas Little Rock, teaching a pro-bono cloud computing management course open to all Arkansas residents. As an author, John co-wrote the 2021 book “Azure Arc-Enabled Kubernetes and Server” from Apress and contributed to four editions of the industry-standard “System Center Operations Manager: Unleashed” from SAMS Publishing (2005-2013). Between 2012 and 2015, he authored weekly cloud and datacenter columns for CBS Technology publications including TechRepublic and ZDNet. A retired U.S. Navy Lieutenant Commander and computer scientist, John worked for NATO in Europe and aboard an aircraft carrier in the Pacific. He earned the Computer Scientist sub-specialty and served as chief of network operations for NATO during the former Yugoslavia conflict. He is also a veteran of the Persian Gulf War. Outside of technology, John’s personal passions include 4-wheeling in his ‘Black Ops’ Jeep Wrangler and running a visionary art clothing company called Lit Like Luma. About the sponsors Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

Welcome to Episode 418 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben sits down with Cat Schneider during a lively conference to discuss a variety of topics, focusing on the theme of “anti-AI.” They reflect on life and technology before AI became prominent, sharing tales of conferences, hackathons, and explorations of older tech solutions. They also discuss some of Cat’s adventures in SharePoint and Power Platform, including managing SharePoint permissions with flows, the challenges of migrating file shares to SharePoint, syncing issues with OneDrive, and practical uses of Power BI for troubleshooting and managing SharePoint data. Additionally, they dive into humorous conference anecdotes from the inaugural Workplace Ninjas US, including accidental late-night adventures. Cat Schneider is an experienced data specialist and Power Platform, SharePoint, and Teams enthusiast with a demonstrated history of innovation for almost 15 years in the public sector. Cat is skilled in Microsoft-based applications, quality assurance, and databases. She is a strong community and social services professional with a Bachelor of Science (B.S.) in Biology from Florida State University. In addition to being a self-taught coder with a never-ending thirst for learning more—and helping others learn and improve their coding skills—she is also co-leader of the Power Platform UX/UI and Accessibility (A11y) Global User Group. 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 Cat Schneider on LinkedIn Yer a wizard, Cat! Cat on GitHub About the sponsors Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!