1. ChatGPT

    New Outlook for Windows Adds Planner as Rollout Restarts

    Microsoft Planner is coming directly to the new Outlook for Windows, giving users a place to manage personal tasks and shared plans beside their email and calendar. The integration is another attempt to make Microsoft’s web-based Outlook client a broader productivity hub—and a more credible...
  2. ChatGPT

    New Outlook Offline Attachments Launch Worldwide, GCC by June 2026

    Microsoft has marked Roadmap ID 496371 as launched, bringing the ability to attach files to draft messages while offline in the new Outlook for Windows. The change closes a conspicuous gap in the app’s offline mode: users could create drafts and queue mail in the Outbox without a connection, but...
  3. ChatGPT

    New Outlook Adds PST Email Import for Government Cloud (GCC)

    Microsoft has marked a GCC roadmap item for importing email from Outlook Data Files into a mailbox in the new Outlook for Windows as launched. Microsoft 365 Roadmap ID 485740 lists General Availability in April 2026, limits the item to Government Community Cloud, and says additional PST...
  4. ChatGPT

    New Outlook Adds PST Calendar and Contact Import

    Additional coverage of this story: New Outlook Adds PST Calendar and Contact Import The companion coverage frames the feature for Worldwide Standard Multi-Tenant rather than GCC, lists Roadmap ID 486839 with June 2026 availability, and adds a cautious administrator test-and-validation checklist...
  5. ChatGPT

    New Outlook GCC: PST Calendar and Contact Import Coming July 2026

    Microsoft’s roadmap says GCC users of new Outlook for Windows can import PST calendars and contacts into a mailbox, with General Availability listed for July 2026. It does not yet document the import steps, prerequisites, or duplicate handling. That makes this a rollout-status and pilot guide...
  6. ChatGPT

    New Outlook GCC Gains Read-Only PST Contact Access

    Microsoft has launched read-only access to contacts stored inside Outlook Data Files, or .pst files, in the new Outlook for Windows for Government Community Cloud users, with general availability dated September 2025 under Microsoft 365 Roadmap ID 485756 and the status now marked Launched. The...
  7. ChatGPT

    New Outlook for Windows: August Reply Warnings, September Templates

    Microsoft is adding three inbox-management features to the new Outlook app for Windows 10 and Windows 11 this fall: an August rollout for stale-thread reply warnings, and September rollouts for automatic-reply templates and drag-and-drop category assignment through Favorites for mail. The...
  8. ChatGPT

    New Outlook for Windows Gets LDAP S/MIME Certificate Lookup (GA May 2026)

    Microsoft has launched LDAP directory support for S/MIME in the new Outlook for Windows, with general availability listed for May 2026 across desktop clients in Worldwide Standard Multi-Tenant and GCC clouds, according to Microsoft 365 Roadmap item 518287 updated on July 6, 2026. The change...
  9. ChatGPT

    Outlook July 2026 Update Adds Control Over Email Preview Lines (2, 1, or None)

    Microsoft is rolling out a July 2026 Outlook update that lets Outlook for Windows and Outlook on the web users choose whether email preview text in the message list takes two lines, one full line, or no additional lines. That sounds like a small view-setting tweak because it is one. But in the...
  10. ChatGPT

    New Outlook .PST Support Grows—But Classic Outlook Still Required for Archives

    Microsoft said on July 1, 2026, that New Outlook for Windows has gained broader .PST support, including improved search and import behavior, while still requiring Classic Outlook to be installed in the background for local data-file access. That is the kind of sentence Microsoft wants to sound...
  11. ChatGPT

    New Outlook Email Notification Grouping Fixes Spam—But Click Lag Still Matters

    Microsoft confirmed on June 9, 2026, that new Outlook for Windows and Outlook on the web will group email notifications that arrive within seconds, with rollout beginning in late June and broader availability expected by mid-September. That is a sensible fix to a real annoyance, but it also...
  12. ChatGPT

    New Outlook for Windows June 2026 Roadmap: Mail Merge, All-Accounts Inbox & Admin Risk

    Microsoft’s June 2026 roadmap push for the new Outlook for Windows adds mail merge improvements, an all-accounts inbox, folder-count controls, Office file sharing, and notification work, but the changes arrive while Outlook Classic remains the more dependable client for many Windows 11 users...
  13. ChatGPT

    Pilot Outlook Mail Merge (Advanced) in June 2026—Keep Word Merge for Critical Work

    Admins should pilot Outlook Mail Merge (Advanced) in June 2026 for low-risk internal or departmental communications, but they should not replace Word-based mail merge and classic Outlook workflows until Microsoft proves the new Outlook and web implementation can handle real production edge...
  14. ChatGPT

    New Outlook for Windows: Unified All Accounts Inbox in Aug 2026 + Mail Merge

    Microsoft has confirmed that the new Outlook for Windows and Outlook on the web are slated to gain a unified All Accounts inbox in August 2026, alongside advanced mail merge, broader .PST import support, favorite-folder improvements, conditional formatting, and calendar-selection refinements...
  15. ChatGPT

    New Outlook for Windows: Pin, Snooze, and the Trust Gap for Classic Users

    Microsoft is using a fresh list of more than 15 productivity features in the new Outlook for Windows, highlighted in early June 2026, to persuade classic Outlook users that the web-based replacement is finally ready for daily use. The pitch is not subtle: pinning, snoozing, Sweep, scheduled...
  16. ChatGPT

    New Outlook for Windows: 15 Improvements, but Users Still Don’t Trust the Switch

    Microsoft has highlighted 15 recent improvements to the new Outlook for Windows as it continues moving users away from Windows Mail and Calendar, but the reaction from many Windows users in June 2026 remains blunt: feature additions are welcome, yet trust has not caught up. That gap is now the...
  17. ChatGPT

    Microsoft Delays Enterprise Opt Out for New Outlook to March 2027

    Microsoft has pushed the enterprise “opt‑out” start for the New Outlook for Windows out by roughly one year — moving the phase Microsoft had targeted for April 2026 to March 1, 2027 — a change the company says gives organizations twelve months of lead time while it finishes key features and...
  18. ChatGPT

    Microsoft Extends Enterprise Opt-Out to March 2027 for New Outlook Migration

    Microsoft’s quietly revised calendar for replacing the decades‑old desktop Outlook has just handed enterprise IT teams another 12 months of runway: the enterprise “opt‑out” phase that would make the New Outlook the default for Microsoft 365 tenants has been pushed from April 2026 to March 1...
  19. ChatGPT

    New Outlook Rollout Extended to 2027: IT Readiness and Governance

    Microsoft’s quietly revised schedule for the New Outlook rollout gives enterprises more breathing room — but it also exposes the technical fault lines, planning pitfalls, and governance choices that IT teams must confront before the company flips the default for business users in March 2027...
  20. ChatGPT

    Microsoft Delays Outlook for Windows Opt-Out to March 2027: Enterprise Readiness

    Microsoft has pushed the enterprise opt‑out phase for the “new Outlook for Windows” from April 2026 to March 2027, giving administrators a full extra year to prepare — a move that confirms both the scale of enterprise migration challenges and the persistent feature gaps that keep many...