Should Our Business Upgrade to Windows 11?

The question has changed since we first wrote this article. It used to be whether Windows 11 was worth the trouble. Since October 14, 2025, when Microsoft stopped issuing security updates for Windows 10, the question for a business is how quickly to get there and what to do with the computers that cannot make the trip. This guide covers what the end of Windows 10 means in practice, which machines qualify for Windows 11, the options for the ones that do not, and a plan for doing the change without a bad week.

What the end of Windows 10 support means

Windows 10 still starts, still runs your software and still connects to the internet. What it no longer receives is the monthly fix for newly discovered security holes. Attackers read the same fix announcements everyone else does, and they scan the internet for machines that have not applied them; an unpatched Windows 10 computer becomes an easier target every month. Three practical consequences follow for a business:

• Insurance. Most cyber-insurance applications now ask whether any unsupported operating systems are in use. A yes raises the premium or brings an exclusion, and the cyber insurance readiness check shows how the rest of the form reads.
• Compliance. HIPAA, PCI DSS and CMMC all expect supported, patched systems. An unsupported operating system is a finding on every one of them.
• Software. Vendors drop Windows 10 from their supported list over time. Microsoft 365 apps, for example, continue to receive security updates on Windows 10 only until October 2028, and other vendors are less patient.

Microsoft offers Extended Security Updates for Windows 10, bought per device by the year, for up to three years. The first paid year ends in October 2026 and each year costs more than the last. It is a bridge for machines that cannot be replaced yet, not a place to live.

Which computers can move to Windows 11

Windows 11 requires a TPM 2.0 security chip, Secure Boot, at least 4 GB of memory and 64 GB of storage, and a supported processor: broadly an eighth-generation Intel Core or newer, a second-generation AMD Ryzen or newer, or a recent Snapdragon. In practice, most business computers bought since 2019 qualify and most bought before 2018 do not. Microsoft’s PC Health Check app gives a yes or no per machine; under a managed IT plan the monitoring agent reports the answer for every computer at once, which is how we plan these projects.

Upgrade, replace or bridge

Every Windows 10 computer in the building lands in one of three groups:

1. Upgrade in place. The machine qualifies and is under four or five years old. The upgrade is free, takes about an hour, keeps programs and files, and can be rolled back for ten days if something misbehaves.
2. Replace. The machine does not qualify, or it qualifies but is old enough that a slow disk and tired battery would make Windows 11 feel worse. Replacing a five-year-old desktop costs less than the wages lost to it; see why computers are slow for the arithmetic. Old machines go to certified recycling with the drives wiped.
3. Bridge. A machine that must stay on Windows 10 for a while, usually because it runs a specialised instrument, a plant-floor controller or an application the vendor has not moved yet. Enrol it in Extended Security Updates, isolate it on its own network, and put a replacement date on the calendar. Our legacy operating system support covers exactly these.

What Windows 11 changes for a business

Day to day, not much: the Start menu is centred, windows snap into layouts, and the interface is calmer. Under the surface the security defaults are better, which is the real reason to move. Hardware-backed protection is on by default, Windows Hello and passkeys replace passwords for many sign-ins, and the platform is where Microsoft’s new work, including Copilot, is happening. Features arrive through annual updates, so a fleet on Windows 11 stays current without another migration.

A plan that avoids the bad week

1. Inventory. List every computer with its age, processor, TPM status and the software it runs. Under managed IT this list already exists.
2. Test the awkward software. Upgrade one machine that runs each line-of-business application, each unusual printer or scanner, and each VPN or remote-access tool. Vendors have had years to prepare, but a few have not.
3. Decide the three groups and order the replacements early; lead times on business laptops still vary.
4. Upgrade in waves, a few machines at a time, outside working hours, with a technician on hand the next morning. Back up first; the rollback works, but a backup is faster.
5. Bridge what remains with Extended Security Updates and network isolation, and put a date on each one.
6. Tell people what changed. A one-page note about the new Start menu prevents a week of “where did it go” calls.

What it costs

The upgrade itself is free. A managed IT plan covers the planning, testing and the upgrades themselves as routine maintenance, priced per computer at the rates on our pricing page. Replacements are quoted separately, and we recommend hardware without commission. Extended Security Updates are bought from Microsoft per device.

Common questions

Is Windows 10 still safe to use?

Not for a business. Microsoft stopped fixing security holes in Windows 10 in October 2025 unless the machine is enrolled in paid Extended Security Updates, and those run out too. Every month without patches adds known, unpatched holes that attackers scan for, and most cyber insurers now ask whether any unsupported operating systems are in use.

How do I know if a computer can run Windows 11?

Run Microsoft’s PC Health Check app, or look at the processor and TPM in Settings. Broadly, computers made in 2019 or later with an eighth-generation Intel or second-generation Ryzen processor and a TPM 2.0 chip qualify; most older machines do not.

Is the upgrade free?

Yes for a licensed Windows 10 computer that meets the requirements. The costs are in the time to test line-of-business software, the machines that have to be replaced, and Extended Security Updates for any that must linger.

Will our software still work?

Almost all mainstream software does. The exceptions are old line-of-business applications, hardware drivers for older printers and scanners, and anything the vendor has stopped updating. Test those first, on one machine, before touching the rest.

What about the computers that cannot be upgraded?

Replace them on a schedule, most urgent first, and enrol the stragglers in Extended Security Updates so they are patched in the meantime. Do not leave them on unsupported Windows 10 and hope; that is the scenario insurers exclude.

Talk to us

If you are not sure how many of your computers are still on Windows 10, we will tell you within a day, with a plan for each one. Call 952-548-5558 or contact us; the first conversation is free and there is no long-term contract.