The Sadly Unfulfilled Promise of the Outlook Calendar Agent
The Outlook calendar agent seemed to be the answer to the difficulties that I sometimes encounter when trying to sort out my schedule. Alas, the agent failed to deliver when it was given guidelines about how I wanted to create appointments. The overall experience makes me consider whether the huge investment Microsoft is making to infuse AI into its products sometimes turns out duds. Like an agent that can’t schedule. https://office365itpros.com/2026/07/07/calendar-agent-disappoints/What’s New in Microsoft 365 Copilot | May 2026
Welcome to the May 2026 edition of What's New in Microsoft 365 Copilot! Every month, we highlight new features and enhancements to keep Microsoft 365 admins up to date with Copilot features that help your users be more productive and efficient in the apps they use every day.
Feature Proposal: OS-level Intelligent Task Organizer (Windows + Copilot)
A Idea about Intelligent Tasks organizer, I have to remember a lot of things during the team meetings like what is been said (we'll schedule a call or follow up etc.,) and what has been communicated in the emails (I'll get back to you after 2 weeks, or call us after two weeks) , And notes that I took in the notepad, or notepad ++,or sticky notes, or word, or one note. I want to chronologically display tasks on the right hand side of the laptop screen just like sticky note and it shall display all tasks one by one, it shall remove tasks are already complete (email sent with confirmation). and arrange, adjust every few mins according to priority/time or user added priority. App shall display small icon (just like chat) upon clicking it shall display ordered list of tasks. and desktop apps like teams/note/word/notepad++,sticky notes can participate by default or other apps like notepad++ can be onboarded manually in to the app. You can use a local model which infers the meaning of “I’ll call you in two weeks” - who is “I”? you or them? “Let’s follow up later” - task or casual statement? “I sent it” - which task did this complete? You can use a local model such that Corporate Teams/Outlook access may allow by corporate policy. Need to put much emphasis on false positives if the app keeps inventing tasks. Do not need to bring big LLMs in to the picture for inference, because of corporate policies may not allow. Microsoft provides operating system,office 365, tools with copilot, the inference can be possible because of all apps/content can be accessible at os level. Problem: Users capture tasks across multiple tools: Teams meetings and chats Outlook emails Notes (OneNote, Notepad, Sticky Notes, Word) Tasks become fragmented, untracked, and often lost. Proposed Solution: A lightweight system-level task layer integrated with Windows + Copilot that: Core Features Automatic task extraction From Teams, Outlook, notes, and user text Example interpretations: “I’ll call you in 2 weeks” “Let’s follow up later” Context-aware inference (local model) Identify: Task owner (“I” vs “you”) Priority signals Deadlines Minimize false positives Chronological task timeline Tasks auto-organized by: Time Priority Recency Floating task panel (desktop UI) Docked widget (like Sticky Notes or chat bubble) Expand/collapse view Always visible option Automatic task lifecycle tracking Detect completion: “Email sent” “File shared” Remove or mark complete automatically Continuous re-prioritization Adjust every few minutes based on: New inputs Deadlines User behavior Privacy-first architecture Use local models (SLM) instead of large cloud LLMs Enterprise admin control for data access Why this matters: Millions of users manually track tasks across fragmented tools, losing productivity daily. This feature would unify task understanding across the OS and M365 ecosystem.Copilot Chat vsus. Microsoft 365 Copilot. What's the difference?
While their names sound similar at first glance, Microsoft 365 Copilot and Microsoft 365 Copilot Chat, they differ in several aspects. And more importantly: one is built on top of the other. What is Copilot Chat (Basic)? First things first. Microsoft 365 Copilot Chat is often simply called Copilot Chat. Copilot Chat (Basic) generates answers based on web content, while Microsoft 365 Copilot (Premium) is also grounded on users' data, like emails, meetings, files, and more. Since early 2025, Microsoft 365 Copilot Chat has been available to all users in organizations, becoming the entry point to AI assistance for many organizations. Copilot Chat (Basic) is the foundational Copilot experience available at no extra cost for everyone with an eligible Microsoft 365 plan, including: Microsoft 365 E3 / E5 Microsoft 365 A3 / A5 Microsoft 365 Business Standard & Business Premium Copilot Chat (Basic) is secured, compliant, and it does not required the full Copilot add-on license. Copilot Chat (Basic) is able to ground responses on: Public web content. Content explicitly shared or work data manually uploaded to the chat by the user. On-screen content or content displayed on-screen in apps like Outlook, Word, Excel, PowerPoint, and OneNote. When it comes to agents, Copilot Chat (Basic) offers these features: You can create your own declarative agents grounded on public web content with Agent Builder. You can use agents built by your org grounded on organizational data with the pay-as-you-go method. There are Microsoft prebuilt agents available like Prompt Coach, however Microsoft premium prebuilt agents like Researcher or Analyst are not included. The screenshot below shows how Copilot Chat looks and highlights its main capabilities. Note the Upgrade button, meaning this is not Microsoft 365 Copilot, but the Copilot Chat (Basic) experience. Note that EDP (Enterprise Data Protection) is available in Copilot Chat (Basic). What is Microsoft 365 Copilot (Premium)? Microsoft 365 Copilot (Premium) is a paid add-on license that builds on top of Copilot Chat and unlocks Copilot's full power. It is available for selected Microsoft 365 plans, including: Microsoft 365 E3 / E5 Microsoft 365 A3 / A5 Microsoft 365 Business Standard & Business Premium With a Microsoft 365 Copilot license, users get everything Copilot Chat (Basic) offers, plus much more: Data grounding: Microsoft 365 Copilot (Premium) includes Copilot Chat grounded on web and/or on user's Microsoft 365 data like emails, meetings, chats, and documents. Office apps: It integrates deeply into Microsoft 365 apps like Outlook, Teams, Word, Excel, and more. The integration includes features like Edit with Copilot allowing Copilot to adjust live your documents or email based on your prompts. Custom agents: It brings the capability to create your own declarative agents grounded in organizational data and/or web data. You can create agent either using Agent Builder or Copilot Studio. MS prebuilt agents: Premium prebuilt agents like Researcher and Analyst are included in Microsoft 365 Copilot (Premium). The screenshot below shows the Copilot chat experience for users who have a Microsoft 365 Copilot license. Note that EDP or Enterprise Data Protection also applies here How can I access Microsoft 365 Copilot Chat? Today, Copilot Chat is accessible via https://m365.cloud.microsoft or https://copilot.cloud.microsoft using your Entra ID (work or school account). One important difference in day-to-day experience: Users with a Microsoft 365 Copilot license typically see Copilot prominently surfaced across Microsoft 365 apps. Users with Copilot Chat only may not see it pinned by default on the Microsoft 365 home page. To improve discoverability, Microsoft 365 Copilot administrators can pin Copilot Chat via the Microsoft 365 admin center, ensuring that users can easily access it without friction. Especially convenient is that if you use the M365 Copilot Chat app on Windows, you can open Copilot using the keyboard shortcut Ctrl + C. What’s the difference? The differences between Copilot Chat and Microsoft 365 Copilot mainly come down to: Licensing Data grounding (web-only vs. personal work data) Integration depth within Microsoft 365 apps I’ve listed the key differences in the comparison below. 👇Top 3 Microsoft Copilot Features You Should Know – April 2026
🚀 Top 3 Microsoft Copilot Features – April 2026 Microsoft Copilot is evolving fast, and keeping up isn’t always easy. That’s why I’ve combined my latest 3 Copilot videos into one short recap, highlighting the top 3 Copilot features that really matter right now 👇 ✅ Practical, real‑world use cases ✅ Focus on productivity in Microsoft 365 ✅ Relevant for knowledge workers, IT pros, and digital workplace teams 🎥 Watch the full video here: 👉 https://youtu.be/W1wzCInpvlQ If you’re working with Microsoft 365 Copilot, Teams, Outlook, or enterprise AI, this overview will help you quickly understand what’s new—and why it matters. 💬 Curious to hear your thoughts: Which Copilot feature is already changing the way you work? #MicrosoftCopilot #Microsoft365 #AIatWork #DigitalWorkplace #Productivity #M365Copilot #EnterpriseIT #CopilotUpdatesMicrosoft Copilot in Outlook: Automate Calendar Instructions & Meetings with AI
🚀 New Copilot Feature in Outlook: Calendar Instructions Microsoft Copilot in Outlook just got smarter. With Calendar Instructions, you can now teach Copilot how you want your meetings handled — and let AI do the heavy lifting. ✅ Set personal scheduling rules ✅ Let Copilot create, move, or update meetings for you ✅ Reduce back‑and‑forth and calendar overload ✅ Stay fully aligned with your preferences In my latest video, I walk through: What Calendar Instructions are How they work in real scenarios Why this is a big step forward for AI‑powered productivity in Microsoft 365 🎥 If you use Outlook daily, this is a feature you don’t want to ignore. 👉 Would you let Copilot manage your calendar automatically? Curious to hear your thoughts 👇 https://youtu.be/iOcwSAHfM0Q #MicrosoftCopilot #Microsoft365 #Outlook #AIProductivity #FutureOfWork #Copilot #M365 #Automation #OutlookTipsIn Case You Missed It: Frontier Transformation and Wave 3 of Microsoft 365 Copilot Announcements
March brought a major set of Frontier Transformation and wave 3 of Microsoft 365 Copilot announcements across Microsoft 365 Copilot, Copilot Chat, and agents—all focused on helping people move faster from intent to action and helping organizations scale AI responsibly. If you missed any of the updates, here’s a quick recap of what’s new and why it matters. Copilot Transforms Knowledge Work These updates deepen how Copilot shows up inside the flow of work—grounded in your content, context, and tools. Word, Excel, and PowerPoint Agents From Copilot Chat, users can ask Word, Excel, or PowerPoint agents to create content, take next steps, or execute tasks, helping them move from intent to action without copying and pasting or switching contexts. 👉 Learn more Edit with Copilot in Word, Excel, and PowerPoint Copilot now creates, edits, and refines content directly inside Word, Excel, and PowerPoint, grounded in the context of a user’s work through Work IQ, so people can iterate and improve content without leaving the app they’re working in. 👉 Learn more Sequences shortened for demonstration purposes. Copilot Chat in Outlook Copilot Chat in Outlook enables users to draft and refine emails, manage calendars and RSVPs, and use the Outlook email widget to take action directly from chat, streamlining everyday communication and scheduling tasks. 👉 Learn more Outlook customer calendar instructions & proactive RSVPs Copilot finds available meeting times, sends invites, and keeps calendars up to date based on custom instructions, notifying users of changes directly in chat to reduce manual coordination. 👉 Learn more Copilot Cowork Built with Anthropic, Copilot Cowork brings a multimodel approach to Microsoft 365 Copilot—so your work isn’t tied to a single model. Cowork moves Copilot beyond prompts into long‑running, multi‑step work. With full awareness of your work context through Work IQ, it lets you delegate meaningful work and stay informed as it progresses. 👉 Learn more Claude Sonnet available in Copilot Chat Users can select Claude models directly in Copilot Chat, alongside next‑generation OpenAI models, bringing leading models from multiple providers into a single Copilot experience. 👉 Learn more Dataverse in Work IQ Work IQ connects signals from Microsoft 365—including documents, meetings, email, and chat—and will soon access operational data in Dataverse through Copilot in Dynamics 365 and Power Apps, bringing work context and business data closer together. 👉 Learn more Work IQ Memory (Chat History) Work IQ Memory enables more relevant, personalized Copilot responses shaped by a user’s work and Copilot chat history over time. 👉 Learn more Extensibility: Work IQ API / MCP Work IQ APIs provide access to production‑ready AI capabilities that work directly with enterprise work context, enabling extensibility through APIs and MCP. 👉 Learn more Launch Demo Copilot in Dynamics 365 & Power Apps Microsoft 365 Copilot is accessible directly within Dynamics 365 Sales, Customer Service, and Power Apps, extending Copilot experiences into business applications where operational work happens. 👉 Learn more Agents That Help Run the Business These announcements focus on building, deploying, and scaling agents across the enterprise. Apps SDK The Apps SDK provides tools to build ChatGPT apps based on the MCP Apps standard, with additional ChatGPT functionality to support agent and Copilot experiences. 👉 Learn more Model Context Protocol (MCP) Apps MCP Apps turn Copilot from a text interface into a governed, interactive execution layer by surfacing interactive app experiences directly in Copilot Chat. 👉 Learn more Apps in Agents: Outlook, Dynamics 365, and Power Apps Agents can bring Outlook, Dynamics 365, and Power Apps directly into chat, allowing users to review information and take action without leaving the conversation. 👉 Learn more Agent Recommendations in Microsoft 365 Copilot When users prompt Microsoft 365 Copilot, the system analyzes intent and recommends an installed, IT‑approved agent directly in the flow of work, making agents easier to discover and use at scale. 👉 Learn more Evaluate agents in Copilot Studio Copilot Studio provides structured, repeatable testing to help catch issues early, reduce the risk of bad answers, and maintain agent quality as agents evolve. 👉 Learn more Visibility, Governance, and Control at Scale As agent usage grows, these updates help organizations move from experimentation to enterprise readiness. Agent 365 Agent 365 serves as the control plane for agents, helping organizations move from experimentation to enterprise‑scale operations by enabling them to observe, govern, and secure agents. 👉 Learn more Microsoft 365 E7: The Frontier Suite Microsoft 365 E7 unifies Microsoft 365 E5, Microsoft 365 Copilot and Agent 365 into a single solution powered by Work IQ and integrated with the productivity apps and security stack customers already rely on. It includes Microsoft Entra Suite and advanced Defender, Intune and Purview security capabilities, delivering comprehensive protection across agents and employees. 👉 Learn more To explore what’s available now—and what’s coming next—visit the Microsoft 365 roadmap and related announcement blogs. 👉 Explore the roadmap
Change Default for Copilot Automatic Room Rebooking Setting in Outlook?
My users with Microsoft 365 Copilot licenses have noticed a newer feature that automatically rebooks meetings with an alternate room if the selected room is unavailable. It appears that this setting is on by default and can be turned off on a per case basis when a new meeting event is being scheduled. Is there a way to turn it off by default and allow people to enable it when a new calendar item is being created instead? Here is what it looks like for me in Outlook. I can click on Edit from the new meeting window and turn it off for a single event. I haven't found a way to change that default behavior. Has anyone found a way to adjust this? Thank you! Brian
