by Scott | May 7, 2026 | Podcast
Podcast: Play in new window | Download (Duration: 32:14 — 22.2MB)
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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.
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Show Notes
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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.
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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. |
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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. |
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by Scott | Apr 23, 2026 | Podcast
Podcast: Play in new window | Download (Duration: 51:49 — 35.6MB)
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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.
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by Scott | Apr 9, 2026 | Podcast
Podcast: Play in new window | Download (Duration: 50:23 — 34.6MB)
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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.
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by Scott | Mar 26, 2026 | Podcast
Podcast: Play in new window | Download (Duration: 34:07 — 23.5MB)
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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.
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by Scott | Mar 12, 2026 | Podcast
Podcast: Play in new window | Download (Duration: 38:41 — 26.6MB)
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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.
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by Scott | Feb 26, 2026 | Podcast
Podcast: Play in new window | Download (Duration: 41:35 — 28.6MB)
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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.
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by Scott | Feb 16, 2026 | Podcast
Podcast: Play in new window | Download (Duration: 34:19 — 23.6MB)
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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.
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by Scott | Jan 29, 2026 | Podcast
Podcast: Play in new window | Download (Duration: 26:41 — 18.4MB)
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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.
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by Scott | Jan 15, 2026 | Podcast
Podcast: Play in new window | Download (Duration: 25:16 — 17.4MB)
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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.
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by Scott | Jan 1, 2026 | Podcast
Podcast: Play in new window | Download (Duration: 38:20 — 26.4MB)
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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.
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