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Microsoft Auto-Installs Microsoft 365 Copilot on Windows
Winsage
June 22, 2026

Microsoft Auto-Installs Microsoft 365 Copilot on Windows

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.
Microsoft reveals how to verify Windows 11's Secure Boot update, what to do if your PC missed it
Winsage
June 21, 2026

Microsoft reveals how to verify Windows 11’s Secure Boot update, what to do if your PC missed it

The expiration of Microsoft's Secure Boot 2011 certificates on June 24 will not prevent older Windows PCs from booting, as confirmed by Microsoft. Devices will continue to operate normally, but they will miss future boot-level security updates, including updates to the Windows Boot Manager and mitigations for newly identified vulnerabilities. The ability to receive the Secure Boot 2023 update depends on the device firmware's compatibility, with many manufacturers, including Dell, HP, Lenovo, and ASUS, having cutoffs for BIOS updates based on the device's End of Service Life. Older PCs using Legacy BIOS or Compatibility Support Module (CSM) mode do not utilize UEFI Secure Boot, making the update irrelevant. Users running Windows 11 on unsupported hardware may have Secure Boot disabled or improperly configured. Without the 2023 certificates, devices cannot receive future revocation updates to the Secure Boot DBX, which lists compromised bootloaders. Users on Windows 10 with supported OEMs may receive the update if a compatible BIOS is available, while those on older PCs without updates can continue using their devices but will lack future security updates. The Secure Boot status can be checked through the Windows Security app, with color-coded badges indicating the status of the certificates.
Microsoft’s AI strategy feels like a beta test — at the expense of Windows and Office
Winsage
June 20, 2026

Microsoft’s AI strategy feels like a beta test — at the expense of Windows and Office

Microsoft has shifted its focus towards generative AI, beginning with its investment in OpenAI in 2019. CEO Satya Nadella has indicated a departure from the company's traditional software-centric vision, emphasizing the need for transformation in light of the AI revolution. The adoption of Windows 11 has been slow, with a survey showing that 30% of HP PCs still run Windows 10, which will reach the end of support on October 14, 2025. Organizations like The Restart Project are helping users transition to Windows 11, while critics argue that Microsoft's upgrade requirements lead to premature obsolescence of functional PCs. Microsoft has launched the Windows K2 program to address user feedback and is exploring an agentic AI operating system. In response to potential EU antitrust fines, Microsoft has unbundled Teams from Office 365, offering a lower-cost option without the collaboration tool. This move has led to a lawsuit from Salesforce, alleging anticompetitive practices. Alternatives like LibreOffice and Euro-Office are emerging, but experts believe they pose limited immediate threats. Additionally, the French government plans to shift from Windows to Linux and replace Microsoft Teams with a domestic platform by 2027. Microsoft's AI initiatives have faced challenges, including backlash over the automatic installation of the Copilot AI app, which was temporarily suspended due to user complaints. Shareholders have filed a class action lawsuit, claiming the company overstated Copilot's success and failed to disclose a revenue decline in Azure. Analysts warn that continued investment in AI without meeting expectations may lead to significant challenges for Microsoft. Reports suggest that Azure was rushed to market, resulting in talent loss and performance issues.
Microsoft's Patch Tuesday update strikes again
Winsage
June 19, 2026

Microsoft’s Patch Tuesday update strikes again

Microsoft has confirmed a bug affecting the Recycle Bin across all supported versions of Windows following its June 2026 Patch Tuesday update. The glitch causes the confirmation dialog to display an "internal" filename instead of the user-friendly filename when deleting files, although the actual file and its deletion process remain unaffected. The issue affects various Windows client and server versions, including Windows 11 (versions 26H1, 25H2, 24H2, 23H2), Windows 10 (versions 22H2, Enterprise LTSC 2021, Enterprise LTSC 2019, Enterprise LTSB 2016), and Windows Server (2025, 2022, 2019, 2016, 2012 R2, 2012). Microsoft is developing a permanent solution, but it is unclear when it will be released. Commercial customers can contact Microsoft Support for Business for a workaround.
Microsoft's latest Windows bug belongs in the Recycle Bin
Winsage
June 19, 2026

Microsoft’s latest Windows bug belongs in the Recycle Bin

Microsoft's recent Windows update has introduced a cosmetic glitch where the confirmation dialog for permanently deleting a file from the Recycle Bin displays the internal naming convention (e.g., $Rxxxxx.ext) instead of the original file name. This issue is limited to the deletion confirmation dialog; the original file name is preserved in the Recycle Bin and displayed correctly upon restoration. Microsoft has acknowledged the problem but has not provided a public workaround, advising organizations to contact Microsoft Support for assistance. A resolution is in progress and will be included in a future update. The glitch affects desktop versions of Windows from Windows 10 Enterprise LTSB 2016 to Windows 11 26H1, as well as Windows Server editions from 2012 to 2025.
Microsoft confirms Recycle Bin bug across all versions of Windows
Winsage
June 19, 2026

Microsoft confirms Recycle Bin bug across all versions of Windows

Reports have emerged about complications from the latest Patch Tuesday update, affecting users with issues such as access problems with OneDrive and Dropbox, BitLocker recovery lockouts, and Blue Screen of Death (BSOD) errors. Microsoft has acknowledged a glitch related to the Recycle Bin after the installation of June's Patch Tuesday update (KB5094126), where the confirmation dialog displays the internal file name instead of the actual name when deleting an item. This issue affects various supported Windows client and server versions, including Windows 11 (versions 26H1, 25H2, 24H2, 23H2), Windows 10 (versions 22H2, Enterprise LTSC 2021, Enterprise LTSC 2019, Enterprise LTSB 2016), and Windows Server (2025, 2022, 2019, 2016, 2012 R2, 2012). Microsoft is working on a solution expected in a future update, but it is unclear if it will be part of the next Patch Tuesday or an out-of-band update. Commercial customers can implement a workaround by contacting Microsoft Support for Business.
My favorite file manager for Windows 11 finally gets a long-requested feature
Winsage
June 18, 2026

My favorite file manager for Windows 11 finally gets a long-requested feature

Files has introduced a new Tree View feature in version 4.1.4, available in the Preview channel, allowing users to visualize folders in an expandable hierarchy. This update enables users to expand drives and nested folders easily. Additionally, the update enhances the Windows Fonts folder, allowing users to preview fonts directly within Files. Version 4.1.3 is also available in the stable release, featuring improvements to the tag system, folder size calculations, and bug fixes. Files can be downloaded from the Microsoft Store or its official website.
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