Microsoft's Extended Security Updates program for Windows 10 is unavailable on some devices due to technical restrictions and regional rollout delays, requiring affected users to upgrade to Windows 11 or accept unpatched systems. Users attempting enrollment may encounter generic error messages such as "We can't enroll you in Extended Security Updates right now. Close this window and try again" or simply "Something went wrong," which provide minimal diagnostic information about the underlying issues.

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Microsoft confirmed a bug affecting Windows 10 systems enrolled in the Extended Security Updates (ESU) program and LTSC editions. The issue causes enrolled devices to display incorrect end-of-support messages despite having active security coverage: "Your version of Windows has reached the end of support. Your device is no longer receiving security updates."

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Windows 10 support ended on October 14, 2025, but organizations can continue receiving critical security updates through the Extended Security Updates (ESU) program. This article explains the technical requirements, procedures, and limitations for deploying ESU licenses in commercial environments using a Multiple Activation Key (MAK).

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Microsoft introduced simplified Windows 11 update titles in late October 2025, removing date prefixes and version information to improve readability. The change faced immediate criticism from IT administrators who found the new naming scheme confusing and impractical for enterprise environments. Within days, Microsoft confirmed it would restore the date format while maintaining other simplifications.

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Microsoft Intune's October 2025 release introduces technical improvements in enrollment reporting, privilege management, and network infrastructure. The updates target enhanced security posture, reduced administrative friction, and improved deployment visibility across Windows Autopilot and Android Enterprise environments.

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The new App Builder and Workflows agents in Microsoft 365 Copilot offer conversational interfaces that allow users to create applications and automate processes using natural language, eliminating the need for traditional development tools. The new agents are available to organizations with Microsoft 365 Copilot licenses enrolled in the Frontier program.

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Windows 11 25H2, now generally available, introduces a native policy for uninstalling pre-installed Microsoft Store apps on Enterprise and Education devices. Initially released in Insider preview in June, this feature eliminates the need for custom scripts, enabling administrators to delete inbox packages through Group Policy or mobile device management solutions. Several months after the June Insider preview, user feedback confirms these limitations remain unaddressed in the general availability release. Users criticize Microsoft's new bloatware removal policy as insufficient and arriving too late, since it excludes the most controversial apps like Edge and OneDrive, while community-created tools have already provided superior removal capabilities for years.

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Microsoft released Windows 11 Insider Preview Build 26220.6982 (KB5067109) to the Dev Channel on October 24, 2025. This update introduces Copy & Search functionality, voice typing configuration options, and proactive memory diagnostics capabilities for improved system reliability.

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VMware Workstation Pro 25H2 introduces calendar-based versioning, a command-line configuration tool, expanded hardware support, and multiple bug fixes. The release adds support for USB 3.2, virtual hardware version 22, and new guest operating systems, including Red Hat Enterprise Linux 10 and Fedora Linux 42. Unfortunately, early adopters have experienced several critical bugs.

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Microsoft is transforming Windows 11 into an AI-powered operating system with deep Copilot integration across the entire user experience. Users can now interact hands-free through Copilot Voice using wake-word activation, while Copilot Vision analyzes on-screen content to provide contextual assistance. The experimental Copilot Actions feature introduces autonomous agents that can perform real tasks on local files, from organizing photos to processing documents. Beyond Windows, Microsoft Edge gains AI capabilities through Copilot Mode, and a new animated character called Mico—reminiscent of the classic Clippy—adds personality to AI interactions.

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Microsoft will discontinue support for Office Online Server on December 31, 2026, ending security updates and technical assistance for the on-premises solution that provides browser-based Office applications. Organizations are encouraged to migrate to Microsoft 365 or use supported desktop clients for SharePoint Server and Exchange Server Subscription Edition deployments.

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Microsoft's October 2025 Windows 11 update (KB5066835) delivers exciting new features alongside critical bugs causing widespread issues. The cumulative update brings AI-powered File Explorer shortcuts, a new "Edit" command-line text editor, and improved multi-monitor support to Windows 11 versions 25H2 and 24H2. However, users report severe problems, including a completely broken Windows Recovery Environment, File Explorer preview pane failures, and localhost connection issues affecting developers. Microsoft has acknowledged these critical bugs and released an emergency patch (KB5070773) to address the most serious WinRE issue. This guide will cover all the new features, known bugs, and solutions you need to know before installing KB5066835.

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Microsoft released the security baseline for Windows 11 version 25H2 on September 30, 2025. The baseline introduces configuration changes focused on network security, attack surface reduction, and legacy protocol elimination. You can download and import a security baseline into Active Directory Group Policy.

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Microsoft Word for Windows has implemented automatic cloud saving for new documents starting with version 2509 (Build 19221.20000). This change affects how users save documents, with all new files defaulting to OneDrive or SharePoint locations. Organizations can control this behavior through Group Policy and Microsoft Intune configurations.

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Windows Server 2025 implements security hardening changes that block WSUS from distributing extended security updates (ESU) to end-of-life operating systems. The modifications affect Windows Server 2012 and 2012 R2 systems receiving ESU updates through WSUS, requiring administrators to implement workarounds or upgrade their infrastructure.

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Microsoft has released the Azure DevOps local MCP Server as generally available, transitioning from public preview to production-ready status. The server enables AI assistants to access Azure DevOps data, including work items, pull requests, test plans, builds, and wikis. This allows IT professionals to automate DevOps workflows through natural language commands while maintaining data security within their local network.

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Microsoft announced new Copilot features for Windows and OneDrive during its third annual OneDrive digital event and a Windows Insider update. The updates introduce AI-powered file management in OneDrive, document creation and export capabilities for Office applications (Word, Excel, PowerPoint, and connectors for third-party services, including Google products.

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Active Directory domain controllers running Windows Server 2025 with the schema master FSMO role may create duplicate schema attribute values when performing Exchange Server schema extensions, causing replication failures across the entire forest. This issue triggers this error message: Error 8418: The replication operation failed because of a schema mismatch between the servers involved. The issue affects environments attempting to deploy Exchange Server cumulative updates or Exchange Server Subscription Edition. Microsoft has acknowledged this as a known issue in KB5065426.

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Microsoft 365 Premium combines productivity applications—Word, Excel, PowerPoint, OneNote, and Outlook—with advanced AI capabilities in a subscription plan launched in October 2025. The plan introduces "vibe working," Microsoft's term for iterative human-agent collaboration in which users guide AI through multi-step tasks to create documents, spreadsheets, and presentations. The subscription consolidates features from Microsoft 365 Family and the discontinued Copilot Pro subscription while introducing exclusive AI agents and elevated usage limits for individual subscribers.

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