The bill just doubled
Windows 10 reached end of support on 14 October 2025. Organisations that weren't ready bought a year of Extended Security Updates (ESU). That year ended on 13 October 2026.
Year two is now live, and Microsoft's commercial pricing doubles each year:
| ESU year | Coverage period | Commercial price per device (USD) | Cumulative if joining late |
|---|---|---|---|
| Year 1 | Oct 2025 to Oct 2026 | $61 | $61 |
| Year 2 | Oct 2026 to Oct 2027 | $122 | $183 |
| Year 3 (final) | Oct 2027 to Oct 2028 | $244 | $427 |
Those are list prices in US dollars before your MSP's margin, GST and currency conversion. For an Australian SMB with 80 laggard devices, year two alone runs to well over A$15,000 at list. That money buys no new capability, only more time.
The catch-up trap
ESU is cumulative. A device that skipped year one can't start at year two. It has to pay for year one as well. So:
- A device that went unpatched for the past year and enrols now costs US$183 before it gets a single update.
- During that unpatched year it was exposed to every Windows 10 vulnerability Microsoft fixed only for ESU customers.
If your MSP's October invoice includes "ESU catch-up" lines, ask the obvious question: why did these devices go a year without patches, and who signed off on that risk?
Where MSPs make money on Windows 10
ESU is a legitimate bridge. It's also an easy profit line. Watch for:
- Margin on licences. Resold ESU often carries a markup. That's normal, but ask for the per-device cost broken out so you can compare it with list.
- "Legacy device management" fees. Some MSPs add a per-device surcharge for Windows 10 machines on top of ESU. Ask what extra work justifies it.
- Slow-walked refresh projects. An MSP paid both ESU margin and a legacy surcharge earns more from delaying your upgrade. Our analysis of hidden MSP costs and all-you-can-eat contract incentives shows how this plays out.
- Hardware upsell on devices that could upgrade. The reverse problem. Some machines that "can't run Windows 11" fail only on a firmware setting (TPM or Secure Boot disabled). Ask for the compatibility report, not just the conclusion.
Questions to put to your MSP this month
- How many of our devices are still on Windows 10, and why is each one still there?
- Which are blocked by hardware, which by application compatibility, and which simply haven't been scheduled?
- What is the per-device ESU cost you're charging, and what is Microsoft's price?
- What's the completion date for the Windows 11 migration? Is it in writing, with a penalty if it slips?
- Did any device run unpatched between October 2025 and now? Is that in the risk register?
- Can any of these workloads move to Windows 365 or Azure Virtual Desktop, where ESU is included?
If the answers are vague, take the conversation to your next contract review. Our contract renewal negotiation guide and SLA negotiation guide show how to tie migration milestones to commercial terms.
The compliance angle
The Essential Eight patch operating systems control expects unsupported operating systems to be replaced. ESU keeps you patched, so it's defensible as a time-limited exception, but auditors and cyber insurers increasingly ask for the end date. A Windows 10 fleet with no retirement plan in year two is the kind of thing that turns up in a claim dispute.
See our Essential 8 Maturity Level 1 guide and the 2026 Essential 8 reality check for how assessors treat legacy systems.
For MSP engineers: this is your leverage
If you're the engineer running the Windows 11 rollout, you're doing revenue-protecting, risk-reducing project work. That belongs on your CV and in your next pay review. Our salary negotiation scripts help you put a number on it, and the technology refresh cycle guide is a useful reference when planning the next wave.
Bottom line
Year two of ESU is the point where waiting costs more than migrating. Every device still on Windows 10 now costs twice what it did last year and will cost twice as much again next October. Ask your MSP for a device-by-device plan with dates. If they can't produce one, that tells you more about the relationship than any QBR slide deck will.
Pricing reflects Microsoft's published commercial ESU list prices in USD. Your actual cost depends on licensing channel, currency and your MSP's margin.
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