Windows 10 end of support arrives on October 14, 2025, which leaves about six months from today. After that date, Microsoft stops releasing security updates for the operating system that still runs on many business PCs. If you have not started planning, now is the time, because hardware lead times and holiday schedules will eat into those months fast.
What Windows 10 end of support means
Your computers will not stop working on October 15. However, they will stop getting security fixes, feature updates, and technical support from Microsoft. Every new vulnerability found after that date stays open on those machines.
That matters for more than security. Cyber insurance applications often ask about unsupported systems, and many compliance frameworks expect supported software. Line-of-business vendors may also stop supporting their apps on Windows 10.
Microsoft lists the date on its Windows 10 lifecycle page. Version 22H2 is the final release, so there is no newer Windows 10 version to move to.
Start with an honest inventory
First, list every Windows device in the organization. Include desktops, laptops, conference room PCs, and the machine in the warehouse that runs label printing. Those forgotten devices are where most plans fall apart.
For each device, record the model, age, processor, and whether it has TPM 2.0. Windows 11 requires TPM 2.0 and a supported processor, so many older PCs simply cannot upgrade. Your management tools should produce most of this data quickly.
Sort devices into upgrade, replace, or retire
Once you have the inventory, sort every device into one of three groups. Devices that meet the requirements and are fairly new can upgrade in place.
Older or ineligible devices need replacement. Some devices, often spares or shared PCs, can simply retire.
In my experience running service delivery, it pays to be strict here. Upgrading a five-year-old laptop to save money often means replacing it a year later anyway. So look at age and condition, not just eligibility.
Budget for the gap, including ESU
Hardware is the largest cost for most organizations. Get quotes early, because supply can tighten as the deadline approaches and many businesses buy at once.
For devices you truly cannot replace in time, Microsoft offers Extended Security Updates. In April 2024, Microsoft announced commercial ESU pricing of $61 per device for the first year. The price doubles each year, to $122 in year two and $244 in year three, and the program runs for up to three years.
Treat ESU as a bridge, not a plan. It buys time for a specialty device or a delayed app, but the cost climbs fast. Also note that Microsoft includes ESU at no extra cost for Windows 10 devices used to access Windows 11 Cloud PCs through Windows 365.
A six-month deadline plan
Here is a simple schedule that finishes before the deadline with room to spare:
- April: complete the inventory and sort devices into upgrade, replace, or retire.
- May: test critical business apps, printers, and peripherals on Windows 11.
- June: finalize the budget, order replacement hardware, and decide which devices need ESU.
- July: upgrade a pilot group and fix problems they report.
- August: roll out upgrades and new devices department by department.
- September: clean up stragglers, wipe retired devices, and update your asset records.
- Early October: confirm every remaining Windows 10 device is either gone or enrolled in ESU.
Test and roll out with care
Test the apps that run the business
Most modern software runs fine on Windows 11. However, older accounting packages, practice management tools, and scanner drivers can cause trouble. Ask each vendor for written confirmation of Windows 11 support.
Then test with real users, not just IT. The person who runs payroll knows which buttons matter. A 30-minute test session with them can prevent a very bad Monday.
Plan the rollout around your people
Upgrades interrupt work, so schedule them thoughtfully. Avoid month-end for finance, busy season for client teams, and fundraising events for nonprofits.
Also prepare staff for the change. Windows 11 moves the Start menu and a few settings. A short guide and a known support contact reduce frustration and help desk calls.
Finally, give each department a date in advance. People handle change better when they know when it is coming and what to save beforehand.
Handle data and old devices safely
Replacing a PC means moving data off the old one. Before any swap, confirm that user files live in OneDrive or another backed-up location, not just on the local drive. Otherwise, someone will lose a folder of important documents.
Next, wipe retired devices properly before you recycle, donate, or sell them. A used laptop with an intact drive is a data breach waiting to happen. Keep a record of each wiped device for your asset list.
Also think about devices that must stay on Windows 10 for a while. Isolate them on the network where you can, limit who logs into them, and track them as exceptions. Windows 10 end of support does not have to mean chaos, but every exception needs an owner and an end date.
How WEBIT approaches this
We start with a device inventory from our management tools and review it with each client, so nobody is surprised by a forgotten PC. Then we build a replacement schedule and budget tied to the client’s broader IT roadmap, instead of a rushed bulk purchase.
Our field engineers handle upgrades and new device setup in planned waves, and we test key apps first. We take no vendor commissions on hardware, so our advice on upgrade versus replace stays honest. You can learn more about our day-to-day support in our managed IT services overview.
Key takeaways
- Windows 10 end of support is October 14, 2025, and security updates stop after that date.
- Inventory every device, including shared and specialty PCs, and check Windows 11 eligibility.
- Use ESU only as a short bridge, since the per-device price doubles each year.
- Test critical apps with real users before the broad rollout.
- Follow a month-by-month plan so the work finishes before October.
Want a second opinion on your Windows 11 migration plan? Talk to an owner.
