Standard support for Windows 10 version 22H2 ended on 14 October 2025. Commercial Extended Security Updates (ESU) are available in three annual periods. Year 1 ends on 13 October 2026; businesses keeping these devices need the appropriate coverage for the next period. LTSC editions have different lifecycles.
If Windows 10 is still in your business, check each device’s enrollment and plan which machines to upgrade, replace, or retain temporarily. October 2026 is the end of commercial ESU Year 1, not the end of the entire program.
The dates and the numbers
Extended Security Updates, ESU, is Microsoft selling you critical security patches for an operating system it no longer supports. For businesses it is bought per device through volume licensing, and the price is designed to make you leave.
Year one: $61 per device, covering through 13 October 2026.
Year two: $122 per device, covering through 12 October 2027.
Year three: $244 per device, covering through 10 October 2028.
After Year 3: the commercial ESU program for Windows 10 version 22H2 ends.
Twenty-five machines: about $1,525 for Year 1, $3,050 for Year 2, and $6,100 for Year 3. $10,675 in total to keep hardware alive that will by then be five to eight years old.
The part that catches people is that the pricing is cumulative. If you skip year one and decide in November that you want coverage, you do not simply start paying year two. You pay for year one as well. Waiting does not save the money. It defers it and adds to it.
Run that across a real office. Twenty-five machines still on Windows 10 costs about $1,525 for Year 1, $3,050 for Year 2, and $6,100 for Year 3, $10,675 in total to keep machines alive that are, by then, five to eight years old. Twenty-five replacement PCs at $900 is $22,500 once, and you own the hardware.
What ESU does not give you
This is where the assumption gets expensive. ESU delivers critical and important security updates. It does not deliver:
- Technical support from Microsoft for anything other than the ESU patches themselves.
- Feature updates or fixes for bugs that are not security issues.
- Application support. Software vendors set their own timelines, and plenty have already stopped testing against Windows 10. When your practice management system or your accounting package drops it, ESU does not help you.
- A compliance answer. If you carry cyber insurance, handle regulated data, or sign vendor security questionnaires, "unsupported operating system with paid patches" is a conversation you will have to have. Have it before renewal, not during a claim.
Ask your IT provider for proof. ESU is not automatic and it is not silent, devices have to be enrolled. Ask to see the enrollment and the purchased coverage period for each device. It is a reasonable question and it takes about a minute to answer.
The Hawaii part
On the mainland this is a purchasing decision. Here it is a logistics decision, and the difference is weeks.
Availability in Hawaii varies. Configured business machines and replacement parts may need to ship from the mainland. Allow time for freight, setup, and a pilot before committing to a fleet-wide change.
The same applies to the machines you are keeping. If a PC needs more memory or a drive to be worth upgrading, that part ships too.
What to do, in order
1. Count what you actually have
Not what you think you have. Every Windows device in the business, its operating system version, its age, and whether it can run Windows 11, which mostly comes down to whether it has TPM 2.0 and a processor on Microsoft's supported list. Any competent IT provider can produce this inventory from monitoring data in an afternoon. If yours cannot tell you how many Windows 10 machines you own, that is its own finding.
The inventory should tell you, per device:
- Windows version and build
- Age and warranty status
- Windows 11 eligible: yes or no
- Who uses it, and what they cannot work without
2. Split the list three ways
Upgrade in place. Machines that are eligible and healthy. This is free, and it is most of a modern fleet.
Replace. Machines that are not eligible, or are old enough that you would be replacing them within two years anyway. Order these first, because of the shipping.
Genuinely stuck. The one PC running the machine that runs the business, a controller for a piece of equipment, a legacy application the vendor abandoned. These exist in almost every business, and they are the real reason ESU is worth buying at all. Isolate them on the network, cover them, and treat them as a project rather than a purchase.
3. Do the stuck ones properly
A machine that cannot be upgraded and cannot be replaced should not simply be left on the same network as everything else with an "it's fine" attached. Segment it, restrict what it can reach and what can reach it, and make sure it is backed up in a way you have actually tested by restoring something.
What not to do
Do not force Windows 11 onto unsupported hardware. There are registry workarounds and they do work, right up until they don't. Microsoft does not guarantee updates for those machines, which puts you in a worse position than Windows 10 with ESU: unsupported and unpatched, with no route back.
Do not upgrade everything on one weekend. Do a pilot group first, including at least one person from each department who uses the business-critical software. You are looking for the printer driver, the scanner, the ancient plug-in nobody mentioned.
Put each annual coverage boundary on your calendar. Confirm the next ESU period or finish migration before that coverage ends, and check the licensing channel’s current terms.
Not sure what you're still running?
We can inventory every Windows machine in your business, version, age, and whether it can take Windows 11, and give you the three lists and a cost either way. No obligation, and you keep the inventory whatever you decide.
Get the inventorySources
Microsoft's own documentation on the program: Extended Security Updates for Windows 10 and Windows 10 end of support.
Questions about your own fleet? Email info@enlightentechhi.com or call 808-451-3630.
Pricing and dates above are Microsoft's published commercial terms checked October 13, 2026. Verify current terms through your licensing channel before you budget.