Four weeks left: the Windows 10 countdown checklist for business
Business Windows 10 security updates end 13 October 2026 unless you pay double for year two. The four-week checklist to land this without a scramble.
If your business bought Windows 10 Extended Security Updates last year, your coverage ends on 13 October 2026 — four weeks from now. Renewing costs roughly double. Here is the checklist for landing this without a scramble.
Windows 10 stopped receiving free security updates in October 2025. Businesses that bought year one of Microsoft's Extended Security Updates (ESU) program got a twelve-month extension — and that extension runs out on 13 October 2026. From that date, every Windows 10 machine without a renewed ESU licence stops receiving security patches entirely, and Microsoft's list pricing means year two costs roughly double year one — about US$122 per device. We covered the deadline itself in Windows 10's second deadline and the free-vs-paid options in our ESU explainer. This post is the practical part: what to actually do in the next four weeks.
Week 1: count your Windows 10 machines — all of them
The first job is an honest inventory. Most businesses that think they have "a few" Windows 10 machines left find more once they look: the warehouse PC, the machine driving a label printer, the laptop a part-timer uses on Thursdays. For each one, record whether the hardware meets Windows 11 requirements (TPM 2.0, a supported CPU) — that single fact splits your fleet into "upgrade in place" and "replace or pay". If you have a managed IT provider, this list should already exist; ask for it.
Week 2: decide the fate of every machine
Every Windows 10 device gets exactly one of four labels:
Upgrade
hardware supports Windows 11: schedule the in-place upgrade before October.
Replace
hardware can't run Windows 11 and the machine matters: order now, because lead times compress badly when everyone buys in the same month. Our procurement service handles sourcing and rollout.
Renew ESU
the machine genuinely can't move yet (a legacy application, a vendor dependency): budget for year-two ESU at roughly double last year's price, and write down the exit plan.
Retire
the machine no one will miss. Decommission it properly: wipe it, remove its accounts, take it off the network.
Week 3: schedule the moves so work doesn't stop
Upgrades and replacements are disruptive if they happen to a person mid-deadline. Batch them: a few machines per day, teams staggered, data and profiles migrated so people sit down to a working machine. This is routine for a provider that does it constantly — our managed IT clients had their Windows 11 migrations planned into business-as-usual months ago.
Week 4: verify, then close the books on Windows 10
The last week is for verification, not new work. Confirm every remaining Windows 10 machine has a current ESU licence attached, confirm upgraded machines are actually patched and healthy, and confirm the retired machines are really gone — a forgotten, unpatched PC that still has network access and cached credentials is exactly the foothold attackers hunt for after a deadline like this.
What about the free consumer ESU?
Microsoft's consumer ESU route — free with a Microsoft account — has been extended into 2027, but it is a consumer program: it does not cover domain-joined or business-managed machines. For a business fleet, the choices remain the four labels above.
Frequently asked questions
What happens if we just keep running Windows 10 after 13 October?
The machines keep working, but every new vulnerability found from that day on stays unpatched forever. Attackers reverse-engineer each month's Windows 11 patches to find the same holes in Windows 10 — so unpatched machines get steadily easier to break into. Cyber insurers also increasingly ask about unsupported operating systems.
Is paying for ESU year two a bad decision?
Not always — for a handful of machines pinned by a legacy application it can be the right bridge. It becomes a bad decision when it's a way to avoid deciding: the price roughly doubles each year precisely to push you off the platform.
Can our old machines run Windows 11 unofficially?
Workarounds exist, but unsupported installs aren't guaranteed to keep receiving updates — which defeats the whole purpose of the migration. For business machines, upgrade supported hardware or replace.
We haven't started. Is four weeks enough?
For most small and mid-sized fleets, yes — if the decisions get made this week. The inventory and the four-label triage take days, not weeks. The thing that makes October painful is starting in October.
The next step
If you'd rather hand this checklist to someone who runs it every week, that's what we do. Call 1300 053 948 or start with our managed IT support page — migration planning is part of the service, not a project fee surprise.
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