Copilot’s Outlook Automation and the $99 AI Plan

What if your Outlook inbox could clean itself up while you focus on bigger projects? Microsoft’s new AI can not only write your emails, it might even reschedule your meetings and finish your slide decks for you. There’s good news for IT admins: recovering from user mistakes just got easier. Microsoft 365 Backup is getting granular restore. And Microsoft is launching a $99-a-month ‘digital employee’ Office plan. It’s a pricey bundle with an AI assistant for everyone, but is it worth the cost?

Thanks to Cayosoft for sponsoring this episode!

Links and resources

• Microsoft 365 Backup to Add Granular Restore Option
• New Microsoft 365 E7 Plan to Bundle Copilot and Agent 365
• Copilot in Outlook: New agentic experiences for email and calendar | Microsoft Community Hub
• Microsoft 365 Copilot Gets New Agentic Experiences, Copilot Cowork Preview

Episode overview

In this episode of This Week in IT, I cover:

• Microsoft rolls out major Copilot improvements in Outlook, including smarter email drafting, better context awareness, meeting triage, rule‑based RSVPs, and proactive schedule optimization.
• New agent mode enhancements arrive across Microsoft 365 apps, enabling whole‑document editing and faster, more capable in‑app AI assistance.
• Microsoft introduces Copilot Cowork, a multi‑step task assistant powered by Anthropic + OpenAI models, designed to autonomously execute complex workflows with user approval.
• Microsoft launches the Microsoft 365 E7 (“First Frontier Suite”) license — a $99/user/month bundle that combines E5, Copilot, Agent 365, security suites, and AI governance tools.
• Microsoft 365 Backup finally adds granular restore for SharePoint and OneDrive, letting admins restore individual files or folders instead of full snapshots.