Windows 10 reached end of support on October 14, 2025. Microsoft no longer ships security patches, no longer fixes bugs, and no longer provides support for the most popular operating system in business history.
And yet, if we walked into ten Houston small business offices today, we would still find Windows 10 running on more than half the machines in some of them. If that’s your business, you’re not alone — but the longer you wait, the worse the math gets.
What "end of support" actually means
Windows 10 still runs. Your applications still open. The login screen still works. So what’s the problem?
The problem is invisible until it isn’t. Every new vulnerability discovered in Windows 10 from October 14, 2025 forward will never be patched. Attackers know exactly which versions of Windows have which unpatched vulnerabilities, and they automate scanning to find them. The risk compounds week over week.
The secondary problem: vendor software is dropping support too. Your accounting software, your line-of-business application, your security tools — their next versions will assume Windows 11. Older versions will keep working until they don’t.
The real risk timeline
In the first months after end-of-support, the risk is manageable. As 2026 progresses, two things accelerate: the number of unpatched vulnerabilities and the automated tooling attackers use to exploit them.
By late 2026 and into 2027, running Windows 10 on a business-grade machine connected to the internet becomes increasingly indefensible — cyber insurers may decline coverage, customers may flag it in audits, and the probability of a successful attack rises sharply.
Upgrade vs. replace vs. extended support
Three paths forward, in order of cost and effort:
1. Upgrade in place. If the hardware meets Windows 11 requirements (most machines made after 2018 do), upgrade is free and takes about 1-2 hours per machine including verification. Risk: if the hardware doesn’t meet requirements, you’ll find out partway through.
2. Replace the device. For machines older than 5-6 years, a clean replacement is usually cheaper than fighting an upgrade. Business-grade laptops in 2026 are $700-1500 depending on specs.
3. Extended Security Updates (ESU). Microsoft sells one-year extensions to security updates for $61/device the first year, doubling each subsequent year. Useful as a bridge for businesses that can’t migrate by deadline, but expensive as a long-term plan.
Costs for a typical 25-seat Houston office
Best case (all machines upgrade-eligible):
- Labor: 25 machines × 90 min × $125/hr = ~$4,700
- Software / licensing: $0 if existing W10 Pro licenses
- Total: ~$5,000
Middle case (half upgrade, half replace):
- 13 upgrades: ~$2,400
- 12 replacements at $1,000 each: ~$12,000
- Labor for setup: ~$3,000
- Total: ~$17,400
Worst case (all replace):
- 25 new laptops at $1,000 each: ~$25,000
- Setup labor: ~$5,000
- Total: ~$30,000
If your business has been deferring this for two years, you’ve already saved nothing — you just shifted the cost to later, when the risk is higher.
Migration scheduling for a working office
For a 25-person office, a sensible schedule:
- Week 1: hardware inventory and upgrade-eligibility check. Identify line-of-business application risks.
- Week 2: pilot migration on 2-3 volunteer machines. Verify all applications work.
- Weeks 3-6: roll out by team or department, 5-8 machines per week.
- Week 7: cleanup, edge cases, kiosk / shared / specialty machines.
If you have machines that absolutely cannot be migrated (specialized industrial software, legacy line-of-business applications), they need to be isolated on a segmented network and not used for general business or web browsing.
What to do this week
- Run a hardware inventory. Which machines are still Windows 10? Which can upgrade?
- Identify the riskiest 5 machines (most internet usage, most sensitive data) and prioritize those first.
- Get a real quote for the full migration. If you don’t have an IT provider, we can run the assessment as part of a discovery call.
- Set a deadline. By when will the last Windows 10 machine be off your network?
Aspendora Technologies provides managed IT services for Houston-area small businesses, including Windows 11 migration planning, hardware procurement, and rollout. Book a discovery call for a no-cost migration assessment.