Three Microsoft support dates land on the same Tuesday: the first paid year of Windows 10 Extended Security Updates for organizations ends, Office 2021 reaches end of support, and the last Windows Server 2012 ESU year closes. Six questions tell you whether it touches you. Every date and dollar figure below is quoted from Microsoft's own lifecycle pages, each one linked.
Microsoft's lifecycle page for Windows 10 Home and Pro:
“Windows 10 will reach end of support on October 14, 2025. The current version, 22H2, will be the final version of Windows 10, and all editions will remain in support with monthly security update releases through that date.”
What Microsoft stopped providing on that date, from its ESU page: technical support, feature updates or new features, and quality updates (including security and reliability fixes). Also from that page: “Windows 10 PCs will continue to work” — they keep running; they stop being patched.
Source: learn.microsoft.com/en-us/lifecycle/products/windows-10-home-and-pro · learn.microsoft.com/en-us/windows/whats-new/extended-security-updatesMicrosoft's lifecycle FAQ lists the three ESU years for Windows 10: Year 1 ends October 13, 2026, Year 2 ends October 12, 2027, Year 3 ends October 10, 2028. Eligible editions per that FAQ: “Enterprise, Education, and Pro in Commercial use”; devices must be running Windows 10, version 22H2.
“Extended Security Updates for organizations and businesses on Windows 10 can be purchased today through the Microsoft Volume Licensing Program, at $61 USD per device for Year One.” … “The price doubles every consecutive year, for a maximum of three years.” … “If you decide to purchase the program in Year Two, you have to pay for Year One too, as ESUs are cumulative.”
Honesty note: Microsoft does not print the Year-Two or Year-Three dollar figure on that page. It says the price doubles; the exact amount, in USD or CAD, is something to check on Microsoft's page or with your licensing reseller before you budget. ESU is sold by the year, not in partial periods. Microsoft also lists Windows 10 virtual machines on Windows 365 and several Azure services as eligible for ESU at no additional cost.
Source: learn.microsoft.com/en-us/lifecycle/faq/extended-security-updates · learn.microsoft.com/en-us/windows/whats-new/extended-security-updatesMicrosoft's consumer ESU page, as fetched on 2026-10-09, says you can enroll “any time until the program ends on October 12, 2027”, with three enrollment options: no additional cost if you are syncing your PC settings, 1,000 Microsoft Rewards points, or a one-time purchase of $30 USD; one licence covers up to 10 devices. It needs Windows 10 version 22H2 and a Microsoft account that is an administrator on the device.
“The consumer ESU program can’t be used in commercial scenarios, and enrollment won’t be offered for: Devices in kiosk mode. Devices joined to an Active Directory domain or Microsoft Entra and/or enrolled in a Mobile Device Management (MDM) solution. However, devices that are Microsoft Entra registered can use the Consumer ESU program.”
So a domain-joined or Intune-managed office PC is on the organization programme above, with its October 13, 2026 year boundary — not the $30 consumer one. If you were counting on the consumer option for a work fleet, that is the first thing to recheck.
Source: microsoft.com/windows/extended-security-updatesMicrosoft's lifecycle page for Office 2021 (Home and Business, Home and Business for Mac, Home and Student, Home and Student for Mac, Professional) shows a retirement date of 10/14/2026 6:59:59 AM Pacific Time — that is the end of October 13, 2026 in Redmond’s time zone. Office LTSC 2021 (Standard, Standard for Mac) shows the same mainstream end date. Neither page lists an Extended Security Update option.
Separately, Microsoft states that Microsoft 365 Apps (the subscription version) running on Windows 10 keep receiving security updates until October 10, 2028, and feature updates until Version 2608 is released — but with reduced support: if an issue occurs only on Windows 10, “support will ask the customer to move to Windows 11.”
Source: learn.microsoft.com/en-us/lifecycle/products/office-2021 · learn.microsoft.com/en-us/lifecycle/products/office-ltsc-2021 · learn.microsoft.com/en-us/microsoft-365-apps/end-of-support/windows-10-supportMicrosoft's lifecycle page for Windows Server 2012 shows extended support ending 10/11/2023 6:59:59 AM Pacific (the FAQ states it plainly: “Windows Server 2012 and 2012 R2 Extended Support ended on October 10, 2023”), followed by three Extended Security Update years. Year 3 runs 10/15/2025 8:00:00 AM to 10/14/2026 6:59:59 AM Pacific; the FAQ prints the Year 3 end as October 13, 2026. The FAQ describes ESU as security updates “up to three years after the product’s End of Extended Support date” — there is no fourth year listed.
After that date a 2012 server is on a 14-year-old operating system with no update programme behind it. The usual places one hides: an old file server, a domain controller nobody wanted to touch, the box a line-of-business application was installed on in 2014, or a virtual machine that was “going to be decommissioned”.
Source: learn.microsoft.com/en-us/lifecycle/products/windows-server-2012 · learn.microsoft.com/en-us/lifecycle/faq/extended-security-updateswinver), every Office 2021 install (File → Account in Word shows the product name), every server still on Windows Server 2012 or 2012 R2 — including virtual machines and the ones nobody logs into. A list with a name against each row is the whole first step; most businesses have never written it down.No. Microsoft’s own ESU page says “Windows 10 PCs will continue to work.” What changes is whether they receive security updates. A PC that was never enrolled in ESU stopped receiving them after October 14, 2025. A PC on organization ESU needs the next year purchased to keep receiving them after October 13, 2026. A PC on the consumer programme is, per Microsoft’s current page, covered to October 12, 2027.
Microsoft says no for the common office set-up: the consumer programme “can’t be used in commercial scenarios”, and enrollment is not offered to devices joined to an Active Directory domain or Microsoft Entra, or enrolled in an MDM solution. Devices that are only Microsoft Entra registered can use it. If your PCs sign in with a company account and are managed, plan on the organization programme.
Microsoft’s page: ESU “enables PCs to continue to receive critical and important security updates through an annual subscription service after support ends.” It does not include new features, customer-requested non-security updates, design change requests, or technical support — “Microsoft will provide support for customers that encounter challenges related to the ESU” itself, nothing more. It is a bridge, not a destination.
Because the three dates are spread across five Microsoft pages, and a business owner should not have to read all five to learn that a Tuesday in October has a cost attached. The page is free and works whether or not you ever call us. If your answer to all six questions is “no, we are already done”, that is a good outcome and you should keep whoever got you there.
No. The page is static HTML and JavaScript. There is no form submission, no fetch call, no analytics on your answers, no email gate, and nothing is stored. You can disconnect from the internet and this page still works.
Honesty note. This page contains no market statistics, no survey data and no figures of our own — every date and price is quoted from the Microsoft pages linked above, and where Microsoft does not print a figure we say so. Your result is arithmetic on your own six answers, nothing more; it is a self-assessment and a planning aid, not an audit, a licensing opinion or legal advice. Prices are Microsoft’s published USD figures and may differ in CAD, by reseller and over time. Windows, Office, Microsoft 365, Microsoft Entra and Windows Server are Microsoft products; Integrated IT Support Inc. is not affiliated with Microsoft.
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