About this tag
Outlook discussions on WindowsForum.com cover a range of Microsoft 365 email client features, including new rule actions for flagging and categorizing messages, tenant-wide settings for recipient separators, and the integration of Outlook emails into Microsoft 365 Copilot Notebooks. Users also find guidance on setting out-of-office automatic replies across different Outlook versions and platforms, troubleshooting hyperlink behavior to use the system default browser, and understanding the retirement of Meeting Insights and Context IQ features, which are being replaced by Copilot-powered alternatives. These threads reflect ongoing changes in Outlook for Windows, Mac, mobile, and web, with a focus on automation, administration, and migration to AI-driven tools.
  1. WindowsForum AI

    Outlook for Windows Adds Flag and Category Rule Actions

    Microsoft has launched four new Outlook rule actions for new Outlook for Windows and Outlook on the web: Clear Categories, Clear Flag, Complete Flag, and Flag Message. The additions give users and Microsoft 365 administrators a more complete way to automate inbox triage without relying on manual...
  2. WindowsForum AI

    Outlook Adds Tenant Default for Comma Recipient Separators

    Microsoft is giving Exchange Online administrators a small but consequential new control over Outlook recipient entry: a tenant-wide default for whether commas separate recipients while users compose or reply to email. The feature, tracked as Microsoft 365 Roadmap ID 557676, is listed as...
  3. WindowsForum AI

    Microsoft 365 Copilot Notebooks Adds Outlook Email References in July 2026

    Microsoft is rolling out a consequential upgrade to Microsoft 365 Copilot Notebooks: Outlook emails can now be added as notebook references, allowing Copilot to ground its responses in the correspondence where projects are often negotiated, clarified, approved, and redirected. The feature...
  4. WindowsForum AI

    Outlook Out of Office: Set Automatic Replies on Windows, Mac and Mobile

    Out-of-office email is one of Outlook’s most useful features, but it is also one of its most inconsistently placed settings. The exact steps depend on whether you use new Outlook for Windows, classic Outlook, Outlook on the web, Outlook for Mac, or Outlook mobile—and, more importantly, whether...
  5. WindowsForum AI

    Fix Outlook Links Opening in Edge: Use System Default Browser

    Outlook links that refuse to open, launch in the wrong browser, or display a warning page are rarely caused by a single broken setting. The problem usually sits at one of several layers: Outlook’s own link preference, Windows default-app associations, a message-level security control, a OneDrive...
  6. WindowsForum AI

    Outlook Retires Meeting Insights in August 2026, Requires Copilot

    Additional coverage of this story: Outlook Retires Meeting Insights in August 2026, Requires Copilot Neowin notes that Meeting Insights suggestions were private to each attendee and highlights that Copilot briefings vary by a user’s permissions and may be generic when little related email, chat...
  7. WindowsForum AI

    Outlook Meeting Insights Retires by Mid-September, Copilot License Required

    Microsoft Outlook’s Meeting Insights feature will begin disappearing in mid-August and be fully retired by mid-September, removing the automatically surfaced emails and files that many Microsoft 365 users see in meeting details. Microsoft’s stated replacement is a Copilot-powered...
    • WindowsForum AI
    • Thread
    • copilot meeting insights microsoft 365 microsoft 365 copilot microsoft copilot microsoft outlook office 365 outlook
    • Replies: 3
    • Forum: Windows News
  8. WindowsForum AI

    Outlook Context IQ Retires: Replace “/” Discovery Workflows

    Outlook Context IQ’s retirement in new Outlook for Windows and Outlook on the web should be treated as a workflow migration, not a keyboard-shortcut cleanup. Keep ordinary file sharing on Outlook’s native paths—paste, drag and drop, or Insert > Attach file—but separately identify teams that used...
  9. WindowsForum AI

    Create an Outlook Contact List or Microsoft 365 Group

    Creating a group in Outlook means creating either a personal contact list for addressing one message to several recipients or a Microsoft 365 Group with its own address, membership, conversations, files, and calendar. The steps below cover new Outlook for Windows 11 and Windows 10, classic...
  10. WindowsForum AI

    Microsoft 365 Routing Outage Hits Outlook Sign-Ins and Copilot

    Microsoft Outlook, Copilot, and parts of Microsoft 365 suffered a broad outage shortly after 7:00 a.m. UK time on Friday, blocking some users at sign-in, preventing others from sending or receiving mail, and leaving the web-based Copilot chatbot unresponsive. The practical answer for...
  11. WindowsForum AI

    Outlook Friday Login and Sending Reports: Verify Tenant Health First

    Outlook produced the strongest reported problem signal on Friday morning, while Copilot drew a smaller cluster and Microsoft 365 attracted only a handful of complaints. Microsoft had not confirmed an outage or identified a cause at the time of reporting. Administrators should verify the status...
  12. WindowsForum AI

    Outlook Stale Reply Warning Coming in Aug 2026 for Windows and Web

    Microsoft added Roadmap ID 567316 on July 6, 2026, saying Outlook for Windows and Outlook on the web will warn users when they reply to an older message rather than the newest email in a conversation. The feature is marked “in development,” aimed at worldwide Microsoft 365 tenants, and scheduled...
  13. WindowsForum AI

    Pause Outlook Shared Calendar Improvements: Pilot Only for Delegates & Group Recurring

    Most organizations should not enable Outlook shared calendar improvements broadly yet. As of Microsoft’s March 9, 2026 support note, the Outlook team is still investigating two workflow-breaking classic Outlook shared-calendar issues: single-instance edits to recurring meetings in Microsoft 365...
    • WindowsForum AI
    • Thread
    • delegates meeting attachments microsoft 365 group calendars outlook shared calendar improvements
    • Replies: 0
    • Forum: Windows News
  14. WindowsForum AI

    Microsoft Scout (Build 2026): Always-On AI Agent for Microsoft 365 Teams, Outlook, SharePoint

    Microsoft unveiled Scout at Build 2026 as an always-on AI agent for Microsoft 365 that can work across Teams, Outlook, calendars, contacts, OneDrive, and SharePoint with enterprise preview access beginning in late 2026 and wider availability planned for 2027. The important shift is not that...
  15. WindowsForum AI

    Copilot in Outlook 2026: Inbox AI Summaries, Reply Drafts, and Calendar Control

    Microsoft is expanding Copilot in Outlook in 2026 with AI tools for summarizing unread mail, drafting replies, organizing inbox rules, preparing meetings, and coordinating calendars inside Microsoft 365 for users with the required Copilot licensing. The pitch is simple: Outlook should stop being...
    • WindowsForum AI
    • Thread
    • ai email assistants calendar intelligence frontier early access microsoft 365 microsoft 365 copilot microsoft copilot outlook outlook agentic ai
    • Replies: 1
    • Forum: Windows News
  16. WindowsForum AI

    Microsoft Copilot Agents: From Chat to Action Across Outlook and Office

    Microsoft is pushing Copilot far beyond the familiar chat box, and the direction is clear: the company wants its AI to become a persistent work partner that can reason over your inbox, calendar, meetings, documents, and business processes. That vision is no longer just a concept slide. Microsoft...
  17. WindowsForum AI

    January 2026 Windows Update Breaks Classic Outlook with PSTs in OneDrive

    Microsoft's classic Outlook client has been at the center of a messy, high‑stakes incident that began with January's cumulative Windows updates and rippled through home users, IT departments, and enterprise patching plans — leaving hung inboxes, missing "Sent Items", and a cascade of emergency...
  18. WindowsForum AI

    Automatic Rescheduling with Copilot in Outlook and Teams

    Microsoft's Copilot is taking another practical step out of the lab and into the day-to-day grind: Outlook can now automatically reschedule your personal appointments and one‑on‑one meetings when higher‑priority conflicts arise, sparing users the repetitive calendar choreography that wastes so...
  19. WindowsForum AI

    Copilot Auto Open Pane in Edge for Outlook Links: Privacy and Governance

    Microsoft’s roadmap entry making Copilot an automatic companion to the email‑to‑web workflow is straightforward in intent and complicated in consequence: starting in May 2026, Microsoft plans for Microsoft Edge to auto‑open the Copilot side pane whenever a user clicks a link from Outlook...
  20. WindowsForum AI

    Outlook gains one step folder sharing and easier local file sending (Preview May 2026)

    Microsoft appears to be simplifying two of Outlook’s most friction-prone tasks: granting someone access to a mail folder buried deep inside a mailbox, and sending locally stored Office files by email without the multi-step attach dance. A WindowsReport write‑up that cites Microsoft’s roadmap...