Microsoft Entra Archives

Winsage

October 8, 2026

Copilot Gets Control of Windows and Your Files as Microsoft’s Recall Bill Comes Due

Microsoft is requesting Windows users to grant its Copilot feature access to their files and activities, following a previous retraction of a similar AI integration due to scrutiny. Copilot can analyze content on the device with user consent, performing tasks like organizing files and troubleshooting, using both local AI models and cloud processing. Microsoft has implemented safeguards, but its security team has raised concerns about potential risks associated with powerful features. The opt-in nature of Copilot places accountability on Microsoft, as users must actively grant access. Hybrid features are set to roll out in the coming months, with taskbar search actions already reaching Windows Insiders. Over 40 percent of new business laptops are being designed as Copilot+ PCs, with the Surface Laptop Ultra scheduled for release on October 16.

Winsage

October 8, 2026

Copilot Gets Control of Windows and Your Files as Microsoft’s Recall Bill Comes Due

Microsoft is inviting Windows users to grant its Copilot feature access to their files and activities, with user consent. The new iteration of Copilot can understand content on the device, perform tasks like organizing files, troubleshooting, and writing code, with some tasks processed in the cloud. Activation is opt-in, folder access is limited, and Copilot operates under separate accounts from users. Microsoft has implemented safeguards, including Microsoft Execution Containers to define agent access. However, internal warnings from Microsoft's security team highlight potential risks associated with agents capable of modifying environments. Features for enhancing auditability of agent activities are under development. Microsoft previously faced criticism for its Recall feature, which raised security concerns. The opt-in design places accountability on Microsoft, as users must grant access. The hybrid features require a Copilot+ PC and are set to roll out in the coming months, with taskbar search actions already reaching Windows Insiders. Over 40 percent of newly manufactured business laptops are Copilot+ PCs, with the Surface Laptop Ultra launching on October 16.

Winsage

October 1, 2026

Windows 10 Users Face a $30 Choice as Microsoft Quietly Extends Security Support to 2027

Microsoft has extended the support cutoff for Windows 10 from October 13, 2026, to October 12, 2027, due to a one-year extension of the consumer security program. Devices enrolled in the Extended Security Updates (ESU) program will continue to receive updates automatically. Unenrolled devices can still enroll until October 12, 2027, to receive critical updates released since their support ended on October 14, 2025. Users in the European Economic Area can access ESU at no extra cost but must maintain a Microsoft account to avoid losing access to updates after 60 days. To qualify for ESU, devices must run Windows 10 version 22H2 in supported editions, have the latest updates, and meet specific criteria. Microsoft 365 Apps and OneDrive on Windows 10 will receive updates beyond ESU, but the operating system itself remains unprotected without ESU. As of August 2026, 25.15 percent of Windows desktops in Germany were still using Windows 10. Users can check their ESU status under Settings, Update & Security, Windows Update.

Winsage

October 1, 2026

Microsoft enables Windows settings backup by default for orgs

Microsoft has updated its Windows settings backup and restore functionality, now automatically enabled for all enterprise systems joined to Microsoft Entra or operating in a hybrid environment after upgrading to Windows 11 version 26H2. The backup tool, previously known as Windows Backup for Organizations, is designed to facilitate the backup and restoration of essential Windows settings for enterprise users during device resets, replacements, upgrades, or reimaging. Originally introduced in November 2024, it became generally available by August 2025. The backup policy will be activated by default for eligible devices following the release of Windows 11, version 26H2 on September 29, 2025, unless administrators have previously configured the policy. The automatic backup feature applies to devices running Windows 11 26H2 in regions not governed by the EU Digital Markets Act and does not require explicit admin configuration for restoring Windows devices. IT administrators can control the backup policy through mobile device management solutions like Microsoft Intune or Group Policy.

Winsage

September 28, 2026

Your PC can get Windows 11 Pro and seven Office apps for just $25.99

A bundle is available that includes Windows 11 Pro and Microsoft Office Professional Plus 2019 for .99, reduced from a regular price of 9. The bundle provides lifetime licenses for both software, designed for a single Windows PC, and does not require a recurring Microsoft 365 subscription. Windows 11 Pro includes features like BitLocker, Hyper-V, and Windows Sandbox, while Office Professional Plus 2019 includes Word, Excel, PowerPoint, Outlook, OneNote, Access, and Publisher. Office 2019 will no longer receive support after October 2025, and Publisher will lose support by October 2026. Windows 11 Pro requires specific hardware compatibility, including TPM 2.0, which can be checked using Microsoft's PC Health Check tool.

Winsage

September 24, 2026

Microsoft: September Windows updates break Always On VPN connections

Microsoft has informed IT administrators about potential connection challenges with the Always On VPN after the September 2026 Windows 11 security updates. Users may face difficulties connecting to their organization's network, particularly if the VPN is set to automatically attempt an alternative connection method upon failure. Symptoms include connections remaining in a 'Connecting' state or displaying the error message: 'The specified port is already in use.' Affected versions include Windows 11, version 26H1 (KB5124012), version 25H2 (KB5124008), and version 24H2 (KB5124008). A temporary workaround involves adjusting the Always On VPN profile from automatic protocol selection to a single protocol (SSTP or IKEv2). Microsoft is also addressing various other issues related to Hyper-V, Remote Desktop Services, USB audio, and the File History backup feature.

Winsage

September 9, 2026

Microsoft Patch Tuesday for September 2026 — Snort rules and prominent vulnerabilities

Microsoft's September 2026 security update revealed 973 vulnerabilities, with 113 classified as critical. Two actively exploited vulnerabilities are CVE-2026-81963 (Windows Update Stack, elevation of privilege, CVSS 7.8) and CVE-2026-85880 (Windows ALPC, elevation of privilege, CVSS 7.8). Among the 113 critical vulnerabilities, 82 are remote code execution (RCE) vulnerabilities. Notable vulnerabilities include: - CVE-2026-69676: RCE in Windows Kerberos, CVSS 8.8, authentication bypass. - CVE-2026-69852: RCE in Windows RRAS, CVSS 7.5, heap-based buffer overflow. - CVE-2026-72957: RCE in Windows Deployment Services, CVSS 7.8. - CVE-2026-69854: Elevation of privilege in Spring Cloud Azure, CVSS 9.0, improper authentication. - CVE-2026-83501: Information disclosure in Windows VBS, CVSS 5.5. - CVE-2026-69730: RCE in Windows DNS Server, CVSS 9.8. Less likely to be exploited vulnerabilities include: - CVE-2026-69845: RCE in Windows DHCP Server, CVSS 9.8, heap-based buffer overflow. - CVE-2026-65772: Vulnerability in Microsoft Dynamics 365 On-Premises, CVSS 8.8, deserialization of untrusted data. - CVE-2026-66302: RCE in Skype for Business, CVSS 9.8. Additional critical vulnerabilities include: - CVE-2026-62916: Elevation of privilege in Microsoft Entra ID, CVSS 9.1. - CVE-2026-83941: Elevation of privilege in Entra ID, CVSS 9.9. - CVE-2026-80098: Vulnerability in Copilot Studio, CVSS 9.3, improper verification of cryptographic signatures. Talos is releasing a new Snort ruleset to detect attempts to exploit these vulnerabilities, with specific SIDs for Snort 2 and Snort 3 rule coverage.

Tech Optimizer

August 26, 2026

How to Protect Against Ransomware: 13 Steps [2026]

Global ransomware attacks increased by 0.8% quarter-over-quarter in Q2 2026. The group Qilin has 279 confirmed victims, maintaining its position as the leading threat actor for four consecutive quarters. The rival group The Gentlemen saw a 62% increase in victims, reaching 269. Checkpoint Research's report indicates a shift in the ransomware landscape, challenging the narrative of declining attacks. IBM's analysis shows breaches within supply chains and third-party vendors have quadrupled over the past five years. Effective ransomware protection requires administrative access to endpoints, firewalls, and backup systems, along with specific software versions and tools. The 3-2-1-1-0 backup strategy is recommended, emphasizing offline, immutable backups. Organizations should implement multi-factor authentication (MFA) across all access points and actively patch known vulnerabilities. Network segmentation is crucial to limit ransomware spread, and canary files can provide early warnings of attacks. Regular phishing simulations and a well-documented incident response plan are essential for preparedness.

Winsage

August 10, 2026

Windows 11 26H2 Ships as an Enablement Package With Movable Taskbar, Local Search, and Default Cloud Recovery

Windows 11 version 26H2 is expected to launch around October 2026 as a small enablement package using the same Germanium platform as versions 24H2 and 25H2. Key enhancements include a movable taskbar, expanded Start menu controls, deeper Copilot integration, and new default cloud recovery settings for managed PCs. Users on versions 24H2 or 25H2 will experience a quick upgrade process requiring only one reboot. The taskbar will allow repositioning and smaller icon sizes, and the Start menu will have new configuration options and privacy settings. Search functionality will prioritize local content, with an option to disable web results. The update will enhance cloud-assisted setup and recovery for eligible Microsoft Entra devices, enabling automatic backup of settings and app lists. Copilot will be integrated into Search and File Explorer, and Windows Security will improve Administrator Protection. The support timeline for 26H2 will reset, offering 24 months for Home and Pro editions and 36 months for Enterprise and Education editions. Hardware requirements remain unchanged, and Arm devices on Windows 11 26H1 will not receive the 26H2 update.

Winsage

August 8, 2026

Windows 11 26H2 is a small update with big quality-of-life improvements, expected around October 2026

Windows 11 will undergo a significant transformation with the upcoming annual update, version 26H2, which introduces enhancements to the interface, search functionality, backup processes, and AI integration. The update will allow users to reposition the taskbar to any edge of the screen and adopt a smaller layout with reduced icon sizes. The Start menu will have new configuration options and a privacy feature for hiding account details during screen sharing. Search functionality will prioritize local content over web results, with an option to disable web results entirely. Cloud-assisted setup and recovery will become a default setting for eligible Microsoft Entra devices, automatically saving configuration settings and app lists. Copilot will be more integrated into daily operations, including a dockable side panel in File Explorer. Updates will also be made to traditional system tools, including a modernized Run dialog and enhanced security for administrator-level operations. The support timeline for Windows 11 installations will reset, with Home and Pro editions receiving 24 months of support and Enterprise and Education editions receiving 36 months. The hardware requirements remain unchanged, and the rollout of 26H2 is anticipated in the latter half of 2026, likely around October.