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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.
Users are complaining that the new Windows version of Outlook is running slowly.
Winsage
June 20, 2026

Users are complaining that the new Windows version of Outlook is running slowly.

Microsoft has introduced two versions of Outlook in Windows 11: Outlook Classic (a Win32 desktop application) and the New Outlook. Users have reported significant performance issues with the New Outlook, noting a lag of approximately 10 seconds for tasks that Outlook Classic performs instantly. The New Outlook operates on WebView2, which involves multiple processes and higher memory consumption, while Outlook Classic runs as a single process. Microsoft is aware of these performance challenges and is testing a new API called 'Delayed Message Timing' to address them. Users find Outlook Classic to be more reliable and faster, particularly for businesses that need efficient notification processing.
Grab no-subscription Microsoft Office apps for only $30, discounted for a limited time
Winsage
June 20, 2026

Grab no-subscription Microsoft Office apps for only $30, discounted for a limited time

Microsoft is offering a lifetime license for Microsoft Office Professional 2021 for Windows at a price of .97, an 86% discount from the regular price of 9.99, as part of their Deal Days event running until June 28. This one-time purchase provides permanent access to essential Office applications, including Word, Excel, PowerPoint, and Outlook, without recurring fees. The software is tied to a single Windows PC and includes instant license delivery and complimentary customer support.
Microsoft Announces New Insider Builds, a Bit of 26H2 News
Winsage
June 19, 2026

Microsoft Announces New Insider Builds, a Bit of 26H2 News

Microsoft has released five new Windows Insider Preview builds and updates for Windows 11 version 26H2. Devices in the Experimental channel will soon update to version 26H2, which can be checked in Settings > System > About or using the winver command. Users in the Beta channel can switch to Experimental via Settings > Windows Update > Windows Insider Program, and can revert back to Beta without reinstalling Windows. PCs on Experimental for versions 24H2 or 25H2 will be upgraded to 26H2, with both versions currently supported. Snapdragon X2-based PCs running Windows 11 on Arm will remain on version 26H1 and will not receive an update to 26H2, but may have a future release potentially called Windows 12. The latest builds are: - Beta (25H2): Build 26220.8690, enhancing reliability of Start, Taskbar, Settings, and virtualization. - Experimental (24H2/25H2?): Build 26300.8697, updating to 26H2 with improvements to File Explorer Copy dialog in Dark mode and reliability enhancements. - Beta (26H1): Build 28020.2308, with minor bug fixes and improved HD Audio driver reliability. - Experimental (26H1): Build 28120.2315, offering similar improvements as the Beta update. - Experimental (Future Platforms, Including Canary 29600 series): Build 29613.1000, enhancing Settings > System > Sounds based on user feedback.
Microsoft Details Windows Clipper Malware Campaign Using USB LNK Worm and Tor-Based C2
Winsage
June 19, 2026

Microsoft Details Windows Clipper Malware Campaign Using USB LNK Worm and Tor-Based C2

Microsoft has identified a Windows-based cryptocurrency clipper campaign that has been active since February 2026. This campaign uses clipboard-intercepting malware with self-spreading capabilities and operates through the Tor network. The clipper malware employs Windows Script Host and ActiveX to launch a Tor proxy and connect to a hidden command-and-control server. It focuses on stealing clipboard data, particularly cryptocurrency wallet addresses, and can exfiltrate screenshots. The malware is distributed via malicious Windows Shortcut (LNK) files on USB drives, which activate a worm that checks for existing infections and fetches the payload from a remote server. The clipper monitors the clipboard every 500 milliseconds for sensitive information and can replace copied wallet addresses with those controlled by attackers. Microsoft recommends behavioral detections, disabling AutoRun for removable media, blocking LNK execution from drives, and monitoring clipboard-related activities as mitigations against this threat.
Microsoft finally admits its default Windows 11 25H2, 24H2 action broke key legacy component
Winsage
June 19, 2026

Microsoft finally admits its default Windows 11 25H2, 24H2 action broke key legacy component

Microsoft released Patch Tuesday updates for Windows 11, specifically KB5094126 and KB5093998, along with dynamic updates KB5094149, KB5095971, and KB5094156. Two issues have been acknowledged: malfunctioning Office applications and complications with the Recycle Bin. In July 2025, Microsoft changed the default settings of Windows 11 to JScript9Legacy in versions 24H2 and later, continuing with version 25H2 in October 2025. This change aimed to enhance security by addressing vulnerabilities related to legacy scripting, particularly cross-site scripting (XSS). A support article details a compatibility issue arising from the transition from jscript9.dll to jscript9legacy.dll, which affects how JScript manages execution context. Functions and definitions established by one script are no longer accessible to subsequent scripts, leading to failures in legacy applications. To address this, Microsoft released the KB5077241 update, which requires manual activation of persistent JScript execution context through a Registry setting. The steps to implement this solution involve creating a feature control registry key and configuring a DWORD value for specific processes or all processes.
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.
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