Still on Windows 10? What the October 2026 Deadline Means for Your Business

Microsoft ended free support for Windows 10 on October 14, 2025. Your Windows 10 computers did not stop working that day, and they will not stop working this October either. What stopped was free security patching. Since then, businesses that stayed on Windows 10 have had one safe path: Microsoft's paid Extended Security Updates program, called ESU.

Here is why we are writing about it now. The first year of that program ends on October 13, 2026. What your business does before that date determines what you pay and how much risk you carry. This is a planning problem, and planning problems are solvable.

What ESU actually is

ESU is a bridge, not a destination. You pay Microsoft per device, and in return your Windows 10 machines keep receiving critical security patches. It does not add features. It does not make old hardware faster. It buys time.

The pricing is designed to push you forward. For business customers, Year 1 costs $61 per device and runs through October 13, 2026. Year 2 doubles to $122 per device and runs through October 12, 2027. Year 3 doubles again. And there is a catch worth knowing: ESU is cumulative. If you skip Year 1 and try to enroll in Year 2, Microsoft requires you to buy Year 1 retroactively. Waiting does not save money. It costs more.

The math on a real office

Say you have 20 computers still on Windows 10. Year 1 ESU is about $1,220. Year 2 is another $2,440. By the end of Year 2 you have spent roughly $3,660 keeping old machines patched, and you still own the same aging hardware. For many offices, that money is better spent replacing the oldest machines on a schedule. For others, ESU is the right short-term call. The point is to do the math on purpose instead of by default.

Why running unpatched is not an option

We will not sell you fear. Here is the plain business case instead. Verizon's 2026 Data Breach Investigations Report found that unpatched vulnerabilities remain one of the most common ways attackers get in. An unsupported operating system stops receiving fixes for newly found holes, and those holes are published for anyone to read. On top of that, cyber insurance applications now ask directly whether you run unsupported software. Answering yes can raise your premium or put a claim at risk. Compliance frameworks ask the same question.

Your three options, honestly compared

• Upgrade in place. If a machine meets the Windows 11 hardware requirements, the upgrade is free and usually smooth. Many machines bought in the last four years qualify.
• Replace on a schedule. Machines that cannot run Windows 11 are typically five or more years old. Replacing them in planned batches spreads the cost and gets you faster hardware in the bargain.
• Enroll in ESU as a deliberate bridge. This is the right call when a critical line-of-business application is not yet certified for Windows 11, or when replacement budget lands next fiscal year. Enroll before October 13, 2026 to avoid paying back-years later.

Most businesses we work with end up using a blend of all three. That is normal and sensible.

How to get ahead of this in August

1. Inventory every Windows machine. You cannot plan around computers you have not counted.
2. Sort them into three buckets: ready for Windows 11, needs replacement, needs ESU.
3. Price each bucket and put it in the 2027 budget now, while budget season is still open.
4. Schedule replacements in batches so no single month hurts.

If you have an IT provider, this is exactly the kind of work they should already be doing for you. If it has not come up, that tells you something too.

Frequently asked questions