Microsoft 365

Winsage
July 1, 2026
By December 2026, support for Microsoft Store versions of Office applications will cease, and they will no longer receive security updates. New feature updates for Microsoft 365 Apps installed via the Microsoft Store stopped in October 2025. Users are encouraged to transition to Click-to-Run versions to maintain access to updates and security features. Click-to-Run allows for immediate application usability while downloading in the background and updates automatically. The Office Deployment Tool (ODT) can assist users in transitioning to Click-to-Run versions.
Winsage
June 28, 2026
Microsoft is refining the Windows 11 interface through the Windows K2 initiative, which includes reducing the visibility of Copilot. In a recent update, Microsoft has discontinued the AI-powered history search feature in Microsoft Edge to prioritize user privacy and security by keeping sensitive data off cloud storage. This change is noted in the Microsoft 365 Roadmap dated June 25, 2026.
Winsage
June 28, 2026
The Italian antitrust authority, AGCM, has launched an investigation into Microsoft 365 for allegedly guiding users toward pricier subscription tiers by integrating AI tools like Copilot and Designer without explicit user consent. Microsoft has stated it will cooperate with the investigation. Last year, Australia’s consumer watchdog made a similar complaint regarding hidden costs related to Copilot during contract renewals. Despite this scrutiny, Microsoft shares rose to €327.90, a 5.71% increase, following a shift in investor sentiment towards AI-software firms. Microsoft also extended its Extended Security Updates (ESU) program for Windows 10 until October 2027, allowing users to delay transitioning to Windows 11, which could hinder hardware sales. The stock remains down nearly 19% year-to-date and is trading below key moving averages. The ongoing regulatory investigation and sluggish Windows upgrade cycle present challenges for Microsoft’s growth.
Winsage
June 28, 2026
Microsoft has resumed the automatic installation of the Microsoft 365 Copilot app on eligible commercial Windows 11 devices that use Microsoft 365 desktop applications. The rollout began in mid-June 2026 and is expected to continue into early July. The app is delivered through the Office updater and is enabled by default, requiring organizations to opt out if they do not want it. This initiative excludes countries within the European Economic Area due to stricter regulations. The move aims to simplify access to AI tools but has faced criticism regarding user consent and control over software installations.
Winsage
June 27, 2026
Microsoft is introducing a feature in New Outlook that groups email notifications to reduce interruptions and notification fatigue. Users have reported that New Outlook is slower than Outlook Classic, with email opening times taking up to 30 seconds compared to just a few seconds in the Classic version. There are also reliability issues with notifications in New Outlook, which can be inconsistent or absent for connected accounts on Windows 10 and 11. Despite the planned improvements, Outlook Classic remains more efficient for managing notifications and opening emails quickly.
Winsage
June 22, 2026
Microsoft has recommenced the automatic installation of the Microsoft 365 Copilot application on eligible commercial Windows devices as of June 2026. The rollout targets devices running Windows 10 (22H2 or later) and Windows 11 with existing Microsoft 365 desktop applications, focusing initially on tenants with Copilot add-on licenses, expected to conclude by late July 2026. Enterprise administrators can manage this installation through a policy titled 'Disable Microsoft 365 Copilot auto-install,' introduced in May 2026. Users can manually uninstall the app, which will not be reinstalled for 90 days if removed. The rollout will not affect the European Economic Area due to exemptions under the Digital Markets Act. This resumption follows a previous halt in March 2026 due to a configuration error and backlash from users regarding the original rollout plan set for October 2025.
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