Episode 427: Copilot Cowork Hands-On Experiences

Episode 427: Copilot Cowork Hands-On Experiences

From Microsoft Cloud IT Pro Podcast by Ben Stegink, Scott Hoag

May 7, 2026 · 32 min

About this episode

The episode discusses hands-on experiences with Copilot Cowork, focusing on data security and custom skills.

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…

People in this episode

Hosts: Ben Stegink, Scott Hoag

Topics covered

  • Copilot Cowork
  • data security
  • hands-on experience
  • Microsoft 365
  • artifact management
  • IRM-protected documents

Keywords

  • Copilot Cowork
  • data security
  • Microsoft 365
  • hands-on experience
  • artifact management
  • IRM-protected documents

Sponsors

TrustedTech Team

Mentioned in this episode

Organizations: YAKO, Anthropic, Microsoft 365, Copilot Cowork

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