Windows 11 Setup to Get Longer for Businesses as Windows 10 Upgrade Nags Intensify

Microsoft is rolling out significant changes to its Windows operating systems, implementing a new security-focused installation process for corporate Windows 11 users while simultaneously increasing pressure on Windows 10 users to upgrade before the older system’s official end-of-life deadline.

A Longer Wait for Corporate Windows 11 Setups

Starting in September 2025, IT departments and corporate users will need to set aside more time for new Windows 11 installations. Microsoft is updating the Out-of-Box Experience (OOBE), the initial setup phase of the OS, in a move that is expected to add approximately 20 minutes to the process. The change is due to the automatic installation of the latest security updates before the user can even access the desktop for the first time.

This new policy, however, will not affect personal computers. It is specifically targeted at “managed” PCs—devices that are remotely administered by a company’s IT department using Microsoft tools like Intune or Autopilot. If you are setting up a personal computer, your installation process will not be impacted by this change.

Security First, Speed Second

Microsoft’s rationale is straightforward: to ensure that new corporate machines are secure from the moment they are first turned on. This preemptive updating prevents a freshly unboxed computer from operating with critical vulnerabilities during its initial hours of use. The system will now automatically fetch and apply all available patches before handing control over to the user. While this is a welcome measure from a security standpoint, it will extend the setup time for IT staff.

Companies will have the option to disable this feature through their configuration profiles if they choose. However, it will be enabled by default for all new installations going forward.

A Diverging Experience for Users

This change in procedure appears to coincide with a major security update planned for September, likely the release of Windows 11 25H2. It creates a split in the user experience: while the setup process is becoming longer and more robust for business clients, it is simultaneously being simplified for home users. Microsoft is streamlining the post-installation “SCOOBE” screen, which often felt intrusive, into a single, more user-friendly panel. This shows a clear, dual strategy: prioritizing upfront security for professionals while focusing on convenience for the general public.

Full-Screen Ads Push Windows 10 Users to Upgrade

Meanwhile, users still running Windows 10 are beginning to encounter more aggressive, full-screen banners urging them to migrate to Windows 11. These intrusive alerts have become more prevalent following the latest Patch Tuesday in August 2025, with user reports linking them to the KB5063709 update.

The pop-up appears after system restarts and updates, warning of the upcoming end of support for Windows 10 and offering to begin the Windows 11 installation immediately. According to user feedback, the alert reappears regularly, even if the “Keep Windows 10” option is selected, making it nearly impossible to ignore.

The Countdown to Windows 10’s End of Life

Microsoft has confirmed that time is running out for Windows 10, with only two major updates remaining before its official end-of-support date on October 14, 2025. After this date, the operating system will no longer receive standard security patches.

The only option for users who wish to continue receiving critical fixes will be to enroll in the paid Extended Security Updates (ESU) program, which will provide support until October 13, 2026. A “Sign up now” button is expected to appear in the Windows Update settings to enable ESU enrollment. However, this option has not yet been rolled out to all users. Microsoft assures customers that the feature is being deployed gradually and will be available on all eligible PCs before the October deadline.