Transition to Windows 11 Archives

Winsage

August 28, 2025

Microsoft releases Windows Backup for Organizations to ease migration of user settings to Windows 11

Windows Backup can back up settings for devices running Windows 10 version 22H2 and Windows 11 version 22H2 or later, but restoration is only available for Windows 11 version 22H2 or newer. Users on Windows 10 cannot restore their settings. The new tool may help organizations transition to Windows 11, especially with Windows 10 support ending on October 14, 2025. To use Windows Backup for Organizations, the August 2025 Windows security update must be applied. Systems are typically Entra-joined, but hybrid joined organizations can also use this feature. The Restore setting is being gradually rolled out, and users may need to wait about a week for it to appear in their Intune tenant. The backup process will occur automatically every eight days.

Winsage

August 27, 2025

Microsoft’s “last-minute snooze button” for Windows 10 is here —sort of

Microsoft will cease support for Windows 10 on October 14, 2025. Users have expressed dissatisfaction with this decision, preferring Windows 10 over Windows 11 due to design flaws and strict system requirements. The public interest group PIRG has petitioned Microsoft to reconsider, warning of increased electronic waste. Microsoft offers an Extended Security Updates (ESU) program for an additional year of support, with a cost structure that has changed to a flat fee for up to 10 devices and requires a Microsoft Account for payment. Users can also use Microsoft Reward points to cover costs or synchronize settings with the cloud for free updates. The enrollment process for the ESU program began in July, but many users have not yet accessed it. The 'Enroll' button for the program is gradually rolling out, with speculation that it may be widely available around September 9, 2025. Organizations have criticized the ESU program as inadequate for the over 400 million PCs that cannot upgrade to Windows 11. The Restart Project argues that Microsoft's approach is a temporary fix that undermines sustainability efforts. The End of 10 group is advocating for users to switch to Linux as an alternative. Microsoft is encouraging upgrades to Windows 11 through notifications.

Winsage

August 27, 2025

The (Microsoft) Windows Are Wide Open for Bad Actors

On October 14, Microsoft will cease support for Windows 10, impacting healthcare organizations that rely on legacy applications. Migrating to Windows 11 typically takes six to nine months and involves creating a new system image, testing applications, re-imaging devices, training staff, and rolling out the new OS. Microsoft will offer an Extended Security Updates (ESU) program for up to three years post-Windows 10 end-of-service, but many organizations struggle with maintaining a Microsoft Enterprise Agreement due to financial issues. Healthcare organizations often use 150 to 300 applications, making them vulnerable to cybercriminals, especially as the end of Windows 10 support approaches, with potential HIPAA violations looming. Cyber insurance implications arise, as claims may be denied if breaches occur due to unsupported systems, leading to increased premiums. Windows 11 includes enhanced security features like TPM 2.0 and a Diagnostic Data Viewer. Cybercriminals are expected to target Windows 10 users after support ends, emphasizing the need for organizations to plan their transition to mitigate risks.

Winsage

August 26, 2025

Microsoft Finally Fixed Windows 10 Free One-Year Extended Security Updates Enrollment Issues

The end of support for Windows 10 is on October 14th, with an option to upgrade to Windows 11 at no cost. Microsoft is offering Extended Security Updates (ESU) for an additional year. Users faced challenges enrolling in the ESU program, with issues reported regarding the "Enroll now" button. An update in August 2025 aimed to fix these issues, but some users still did not see the enrollment option. Enrollment options for ESU include backing up settings to a Microsoft account, using Microsoft Rewards points, or making a one-time payment. Windows 11 installation is possible on any Windows 10 machine, and detailed instructions are available for bypassing hardware verification.

Winsage

August 26, 2025

Can’t sign up for extended Windows 10 support? Don’t panic, the rollout is underway – but it’s reportedly going ‘slowly’

Microsoft is rolling out an extended support offer for Windows 10 users, allowing them to continue using the operating system without the immediate need to upgrade to Windows 11 before the End of Life deadline in October 2025. The enrollment wizard for extended security updates (ESU) will eventually be available to all Windows 10 PCs, but many users have not yet seen this option in their Windows Update panel. Reports indicate a slow rollout, causing uncertainty among users regarding their eligibility. Microsoft has increased notifications encouraging users to transition to Windows 11, particularly as the October deadline approaches. Users can opt for free access to ESU by syncing their PC settings to OneDrive, pay a nominal fee, or redeem 1,000 Microsoft Rewards points for access.

Winsage

August 25, 2025

Windows 10’s latest update adds big nag screens for Windows 11 for some people

Users of Windows 10 must decide whether to extend support, switch to an alternative operating system, or upgrade to Windows 11, as support for Windows 10 ends on October 14th. Microsoft is encouraging users to transition to Windows 11 through a full-screen prompt introduced in the August update, which continues to appear even if users choose to stay on Windows 10. The company aims to create urgency for upgrading as the deadline approaches.

Winsage

August 25, 2025

Microsoft slowly rolls out a button allowing Windows 10 users to refuse Windows 11

Microsoft is ending support for Windows 10 on October 14, 2025, and has introduced an Extended Security Updates (ESU) program that allows individual users to pay for continued security updates. A new feature will soon appear in the Windows Update section of the Settings menu to facilitate enrollment in the ESU program, which will be accessible to all users before the end-of-life date. Users can still enroll in the ESU program for a year after the support ends, even if they see the enrollment button after the deadline. Standard users will need to pay annually for these updates, but there are alternatives to access ESU, such as syncing settings to OneDrive or using Microsoft Rewards points.

Winsage

August 24, 2025

Microsoft Warning—Do Not Update Windows Until You Read This

Microsoft users are experiencing multiple issues related to the latest security update. An emergency update was released to fix a critical problem causing Windows PCs to potentially fail during a reset. Users are advised to use this out-of-band update instead of the standard KB5063875. Additionally, there is a problem with SSDs disappearing when large files are written, which is under investigation, and users are recommended to delay large file transfers. A third issue involves performance problems, such as severe stuttering and lag, when using Network Device Interface (NDI) for streaming after the August security update. Microsoft is investigating this and suggests users adjust the NDI Receive Mode settings. Users are encouraged to check Microsoft's updated guidance on known issues before proceeding with the update.

Winsage

August 24, 2025

Microsoft nags more users with Windows 10 end of life banner, says get Windows 11

Users on Windows 10 are experiencing persistent upgrade reminders following the August 2025 Patch Tuesday update (KB5063709), which includes a full-screen banner encouraging them to upgrade to Windows 11. This pop-up appears after updates are installed and indicates that support for Windows 10 will end on October 14, 2025, after which users will not receive technical support or security updates. Users can choose to dismiss the alert, but it will reappear, along with options to download or schedule the installation of Windows 11. Microsoft has updated its documentation urging users to make a decision before the end-of-life date. After October 14, 2025, Windows 10 will receive only two updates, and users can extend updates until October 13, 2026, by using the 'Enroll now' button on the Windows Update page, though this option may not be available to all users. It is recommended that users save a copy of the Windows 10 ISO before the end-of-life date.

Winsage

August 22, 2025

Get Windows 11 Pro before Microsoft ends support for Windows 10

Microsoft is discontinuing support for Windows 10, prompting users to decide between staying on an outdated system without security updates or upgrading to Windows 11 Pro, which is currently priced at .97, down from its usual price of 9. Windows 11 Pro features a refreshed interface, Snap Layouts for window organization, virtual desktops, optimized resource management for better performance, and enhanced security measures including BitLocker encryption and biometric login options. It also includes advanced features like DirectX 12 Ultimate, Hyper-V, Windows Sandbox, and Microsoft Copilot. The upgrade provides a lifetime license and ongoing updates as long as the hardware is supported, but the promotional price may not last.