Microsoft’s slow, staged rollout of the Windows 10 Enroll now (ESU) wizard means the extension lifeline Microsoft promised for legacy PCs is available — but not instantly visible to everyone, and it comes with conditions and caveats that every Windows 10 user should understand before relying on it.
Microsoft set the official end-of-support date for Windows 10 as October 14, 2025, but followed that with a one-year Extended Security Updates (ESU) program for consumers that delivers security-only updates through October 13, 2026. The consumer ESU program was surfaced in Windows Update as an enrollment wizard labeled “Enroll now” and offers three enrollment routes: enabling Settings sync (free), redeeming 1,000 Microsoft Rewards points (free), or a one-time purchase of $30 USD (per account, covering up to ten devices). These consumer details are documented in Microsoft’s official ESU support guidance. (support.microsoft.com)
Public reporting and forum testing show the UI and flows exist in production, but Microsoft has phased the rollout and patched early bugs that caused the wizard to crash for some users. That staged rollout is why many users still report they do not see the Enroll now toggle in Settings > Update & Security > Windows Update. Independent coverage and testing confirm that installing the latest cumulative updates and meeting the documented prerequisites usually resolves the visibility and enrollment failures. (support.microsoft.com, learn.microsoft.com)
Independent testing and press coverage found the Enroll now flow functioning in some updated machines, while other users reported the option missing entirely. WindowsLatest’s reporting — which drove this particular user question — quotes Microsoft saying the toggle will be visible to everyone before the EOL deadline, but also confirms the wizard is being rolled out slowly. That phrasing aligns with Microsoft’s staged rollout approach but represents a company promise rather than a measurable, universal condition that can be independently verified for every device today.
That requirement has two important implications:
However, the program’s reliance on Microsoft Accounts, the security-only scope, and the phased rollout create real trade-offs. ESU is a stopgap, not a substitute for a long-term migration strategy. The staged visibility and early wizard instability are reminders that critical lifecycle features still require careful rollout and robust QA when exposed to millions of consumer PCs. Users should treat ESU as a one-year breathing space, not a license to defer planning indefinitely. (support.microsoft.com)
Windows 10’s extra year of security updates is a welcome reprieve for many, but it’s not a panacea. The enrolment wizard’s phased rollout and account requirements mean that some users will enjoy a frictionless path to safety, and others will need patience or alternative arrangements. The prudent course is simple: update now, enroll if you need one more year of protection, and use the time ESU buys you to plan and execute a clean migration strategy before October 13, 2026. (support.microsoft.com, learn.microsoft.com)
Source: windowslatest.com Hate Windows 11? Windows 10's extended updates Enroll button is slowly rolling out, says Microsoft
Background / Overview
Microsoft set the official end-of-support date for Windows 10 as October 14, 2025, but followed that with a one-year Extended Security Updates (ESU) program for consumers that delivers security-only updates through October 13, 2026. The consumer ESU program was surfaced in Windows Update as an enrollment wizard labeled “Enroll now” and offers three enrollment routes: enabling Settings sync (free), redeeming 1,000 Microsoft Rewards points (free), or a one-time purchase of $30 USD (per account, covering up to ten devices). These consumer details are documented in Microsoft’s official ESU support guidance. (support.microsoft.com)Public reporting and forum testing show the UI and flows exist in production, but Microsoft has phased the rollout and patched early bugs that caused the wizard to crash for some users. That staged rollout is why many users still report they do not see the Enroll now toggle in Settings > Update & Security > Windows Update. Independent coverage and testing confirm that installing the latest cumulative updates and meeting the documented prerequisites usually resolves the visibility and enrollment failures. (support.microsoft.com, learn.microsoft.com)
What Microsoft is offering — the essentials
- Duration: ESU extends critical and important security updates for Windows 10 devices from October 15, 2025 through October 13, 2026. This is security-only coverage; feature updates and general technical support are not included. (support.microsoft.com)
- Enrollment routes (consumer):
- Free: enable Windows Backup / sync PC settings to a Microsoft account (the “no-cost” option).
- Rewards: redeem 1,000 Microsoft Rewards points.
- Paid: make a one-time purchase (Microsoft lists ~$30 USD) that can apply across up to 10 devices tied to the same Microsoft Account. (support.microsoft.com)
- Eligibility: Devices must be running Windows 10, version 22H2 (Home, Pro, Pro Education, Workstation) with the latest cumulative updates; the Microsoft Account used to enroll must be an administrator account and cannot be a child account. Certain device scenarios (domain-joined, MDM-managed, kiosk mode) are not eligible for the consumer ESU flow. (learn.microsoft.com, support.microsoft.com)
The rollout, the bug, and why you might not see the button yet
Microsoft has rolled the ESU wizard into production in phases. That staged approach means some eligible machines will show the Enroll now link in Windows Update, while others — even fully patched, eligible devices — may not see the link yet. Microsoft’s release notes and cumulative update history document a specific fix: an August cumulative update addressed a bug where the enrollment wizard would open, begin loading, and then close unexpectedly. Users who experienced that crash often regained enrollment capability after installing the August cumulative update. (support.microsoft.com, learn.microsoft.com)Independent testing and press coverage found the Enroll now flow functioning in some updated machines, while other users reported the option missing entirely. WindowsLatest’s reporting — which drove this particular user question — quotes Microsoft saying the toggle will be visible to everyone before the EOL deadline, but also confirms the wizard is being rolled out slowly. That phrasing aligns with Microsoft’s staged rollout approach but represents a company promise rather than a measurable, universal condition that can be independently verified for every device today.
How to check eligibility and enroll (practical step-by-step)
If you want to know whether your Windows 10 PC can enroll, follow these steps in order. This is the fastest, lowest-friction approach to check and enroll when the wizard reaches you.- Verify Windows version: open Settings → System → About and confirm you are running Windows 10, version 22H2. If not, install all available updates and upgrade the device to 22H2. (learn.microsoft.com)
- Install latest cumulative updates: run Settings → Update & Security → Windows Update → Check for updates and install all pending cumulative updates. The August 12, 2025 cumulative update (listed as KB5063709) included fixes tied to ESU enrollment stability. Installing the latest updates eliminates the common enrollment blocker. (support.microsoft.com)
- Sign in with a Microsoft Account (if not already): the consumer ESU license is tied to a Microsoft Account. If you use a local account, the ESU enrollment flow will prompt you to sign in. Administrator privileges are required. (support.microsoft.com)
- Open Settings → Update & Security → Windows Update and look for the Enroll in Extended Security Updates link (usually located near the Check for updates button). Click Enroll now and follow on-screen prompts to choose a path (sync settings, redeem Rewards, or purchase). (support.microsoft.com)
What ESU covers — and what it doesn’t
- ESU covers only security updates that Microsoft classifies as Critical or Important. It intentionally excludes feature updates, non-security quality patches, and technical support. That means you will still miss out on bug fixes unrelated to security and any new functionality introduced to Windows 10 beyond the ESU scope. (support.microsoft.com)
- ESU is a temporary bridge — not a permanent solution. The consumer program is limited to one additional year. Organizations that need longer support have separate commercial ESU arrangements available under different terms. (learn.microsoft.com)
Why Microsoft requires a Microsoft Account — and why that matters
Microsoft’s consumer ESU options are explicitly tied to a Microsoft Account for enrollment. The company ties the ESU license to the account so a single purchase or redemption can be associated with up to 10 devices. That design decision explains why even paid enrollments require signing in: account-based licensing enables the multi-device benefit and reduces fraud/abuse of the free/Rewards routes. (support.microsoft.com, learn.microsoft.com)That requirement has two important implications:
- Privacy & telemetry: users who were holding out against cloud sync and Microsoft Accounts now face a choice: accept account-based management (and cloud syncing) to enroll for free, or pay and still need to sign in to tie the ESU license to a Microsoft Account. Some outlets and privacy advocates warned users that requiring sign-in even for paid ESU put pressure on local-account loyalists. (techradar.com, windowscentral.com)
- Local-account friction: households that prefer local accounts must either convert a device to a Microsoft Account for enrollment or accept the paid path that also requires signing in during the process. That weakened the “pay and stay local” expectation many assumed would remain. Independent outlets flagged this as a controversial catch in Microsoft’s messaging. (techradar.com)
Troubleshooting checklist
If the Enroll now option is missing or the wizard fails, try the following in order:- Confirm Windows 10 version 22H2 and install all pending updates. Microsoft’s ESU enrollment requires the target release and certain security rollups. (learn.microsoft.com)
- Install the August 12, 2025 cumulative update (or later) — the KB that contains fixes for the enrollment wizard crash. Reboot and re-check Windows Update. (support.microsoft.com)
- Sign in with a Microsoft Account that is an administrator on the machine; child accounts are not valid enrollment endpoints. (support.microsoft.com)
- Ensure the device is not domain-joined or managed by an enterprise MDM solution; consumer ESU is intended for personal devices only. (support.microsoft.com)
- If the UI still does not appear, be patient: the enrollment wizard is being rolled out in phases and may take time to reach every eligible device. WindowsLatest’s reporting and forum tests correspond with this phased visibility.
The broader technical and security context you should not ignore
- Secure Boot certificate expiration: Microsoft’s August cumulative update notes include a caution about Secure Boot certificate expiration starting June 2026. That is separate from ESU but can affect a device’s ability to boot securely if system firmware and certificate chains are not updated. Users and admins should review Microsoft’s guidance on Secure Boot certificate transitions and prepare accordingly. This is not an ESU-specific issue, but it is an adjacent lifecycle risk that matters to devices you plan to keep in service. (support.microsoft.com)
- App-layer protections persist: Microsoft has indicated that certain app-level protections (for example, Microsoft 365 Apps security updates and Microsoft Defender signature updates) will continue under separate lifecycles beyond Windows 10’s EOL, but those protections are not a substitute for OS-level security updates. ESU protects the OS attack surface; Defender and app updates protect specific product layers. Relying on app protections alone still leaves OS vulnerabilities unpatched.
Strengths of Microsoft’s approach (what’s good)
- Low-friction consumer option: For households with multiple older PCs, the paid ESU option that covers up to 10 devices for a single $30 purchase is an economical short-term fix compared with buying multiple new PCs. The free route (sync settings) or Rewards redemption provides multiple, accessible enrollment choices. (support.microsoft.com)
- Rollout by Windows Update: Integrating the ESU enrollment UI directly into Windows Update simplifies the process for non-technical users. Microsoft pushed fixes through cumulative updates to stabilize and scale the experience. (support.microsoft.com, learn.microsoft.com)
- Time to plan: ESU buys consumers and smaller households time to plan, budget, and migrate at a manageable pace rather than forcing immediate hardware replacement for all older devices. This reduces abrupt obsolescence pressure for many users. (tomsguide.com)
Risks, downsides, and things to watch closely
- Account-tethered licensing: The requirement to use a Microsoft Account for enrollment — even when paying — removes a hardline local-account escape route for privacy-minded users. That is a deliberate trade-off that ties the license to an account rather than to machine-only activation keys. Expect criticism and possible legal/policy challenges around this condition. (techradar.com)
- Security-only scope: ESU only delivers security updates — not feature or non-security quality fixes. That means certain stability bugs or compatibility fixes will not arrive even if they impair day-to-day use. Relying on ESU for more than a year risks accumulating technical debt. (support.microsoft.com)
- Phased visibility and fragile UX: The early wizard crash and phased rollout mean some users may be caught in limbo — eligible but unable to enroll right away. A device that appears to “work” without visible enrollment may simply not be receiving the assurances Microsoft promises until the wizard reaches it. (support.microsoft.com)
- Full-screen ads and upgrade nudges: Microsoft’s push to upgrade users to Windows 11 has included full-screen upgrade prompts and other aggressive upgrade notifications. Expect those prompts to persist for some users who remain on Windows 10 despite ESU enrollment; enrollment does not remove upgrade advertising. Independent reporting and user complaints have called out increased ad/upgrade nudging in recent months. (techradar.com)
- Environmental and legal scrutiny: Public commentary and at least one consumer legal action have framed Microsoft’s EOL timetable as controversial for environmental, disclosure, and consumer-protection reasons. That debate is ongoing and could shape future policy or consumer remedies. These are litigated and public-policy issues rather than technical ones; they illustrate reputational and regulatory risk.
Recommended plan of action (short- and medium-term)
- Immediate (0–30 days)
- Confirm which machines are mission-critical and inventory OS versions.
- For devices remaining on Windows 10, ensure they are updated to version 22H2 and install the latest cumulative updates (including the August 2025 rollups). (learn.microsoft.com, support.microsoft.com)
- If you want ESU, sign in with a Microsoft Account (or create one), check Windows Update for the Enroll now prompt, and enroll using the path that best fits your privacy and budget needs. (support.microsoft.com)
- Near-term (1–6 months)
- Make a firm migration plan for each device: upgrade in-place to Windows 11 where supported, or schedule hardware replacement for incompatible systems. ESU should be a bridge, not a permanent choice. (tomsguide.com)
- Assess third-party software and peripheral compatibility with Windows 11 and with expected security-only maintenance patterns on Windows 10.
- If you manage devices for others, document which ones are enrolled in consumer ESU and tie them to the appropriate Microsoft Account per the licensing model.
- Long-term (by October 13, 2026)
- Complete migrations off Windows 10 or make arrangements for continued enterprise-level support where necessary. ESU coverage ends on October 13, 2026; do not treat ESU as a multi-year maintenance plan. (support.microsoft.com)
Verdict — is ESU a sensible fallback?
Yes — with conditions. For households and small users who cannot upgrade immediately, the consumer ESU program provides a practical, low-cost bridge that can materially reduce risk for another year. Microsoft’s integration of ESU into Windows Update is a usability win, and the multiple enrollment paths (free, Rewards, paid) make it flexible for different user preferences. (support.microsoft.com, windowscentral.com)However, the program’s reliance on Microsoft Accounts, the security-only scope, and the phased rollout create real trade-offs. ESU is a stopgap, not a substitute for a long-term migration strategy. The staged visibility and early wizard instability are reminders that critical lifecycle features still require careful rollout and robust QA when exposed to millions of consumer PCs. Users should treat ESU as a one-year breathing space, not a license to defer planning indefinitely. (support.microsoft.com)
Final notes and cautionary flags
- Microsoft’s official ESU documentation and the KB release notes should be your primary references when making enrollment decisions; they contain the precise eligibility rules and update prerequisites. Confirm your device’s version and installed KBs before assuming enrollment will be available. (support.microsoft.com)
- Public reporting (including WindowsLatest and other outlets) correctly captured the rollout’s phased nature and the account-tethered licensing caveat; those reports are useful for understanding user experiences and edge-case behaviors, but they are secondary to Microsoft’s published support articles. Where reporting quotes Microsoft directly about “rolling out to everyone,” treat that as a company statement about intent and timing rather than an empirical guarantee that every eligible device will see the UI immediately.
- If you manage sensitive or compliance-bound systems, plan for enterprise ESU options or migration strategies that align with regulatory needs; consumer ESU is not suitable for domain-joined or MDM-managed enterprise fleets. (learn.microsoft.com)
Windows 10’s extra year of security updates is a welcome reprieve for many, but it’s not a panacea. The enrolment wizard’s phased rollout and account requirements mean that some users will enjoy a frictionless path to safety, and others will need patience or alternative arrangements. The prudent course is simple: update now, enroll if you need one more year of protection, and use the time ESU buys you to plan and execute a clean migration strategy before October 13, 2026. (support.microsoft.com, learn.microsoft.com)
Source: windowslatest.com Hate Windows 11? Windows 10's extended updates Enroll button is slowly rolling out, says Microsoft