What if a core tool you rely on—your EHR at a clinic in Oak Park, the SIS at a Bronzeville charter school, the claim system at a Schaumburg brokerage, a township laptop, or a donor database on the West Side—suddenly stopped being safe to use?
That’s where many small and midsized Chicago-area organizations are headed with Windows 10.
The clock is ticking
Microsoft’s free support for Windows 10 ends October 14, 2025. That’s weeks away—not nearly enough time if you still need to scope, budget, test, and roll out upgrades across your fleet.
And when support ends, it truly ends:
- No more security patches
- No more bug fixes
- No help from Microsoft when something breaks
Yes, your PCs will still start. But you’ll be running unpatched systems—prime targets for cyberattacks.
Worse, awareness is low. Recent surveys show 18% of business leaders don’t know support is ending, and another 14% know but haven’t started planning. That’s a lot of risk sitting on a lot of desks.
“Can’t we just pay for extra updates?”
Microsoft’s Extended Security Updates (ESUs) exist—but they’re
- not free,
- per-device, and
- get pricier every year.
ESUs buy time; they don’t fix the underlying problem.
The smarter move: Windows 11
Windows 11 isn’t a coat of paint—it’s a safer, faster platform designed for modern work:
- Built-in security hardening to help defend today’s threats
- Smoother performance and tighter integration with Teams, OneDrive, and Copilot
- Features that actually help hybrid teams get things done
The compatibility catch
Not every Windows 10 device can make the jump. Many older machines miss hardware requirements for Windows 11. That can mean a hardware refresh—another reason to start now instead of making last-minute, expensive decisions.
Why this matters extra in our markets
- Healthcare: Unsupported systems can jeopardize HIPAA compliance and patient safety.
- Education: FERPA and state data rules expect up-to-date, supported platforms.
- Insurance: Carriers increasingly require supported OSes for cyber coverage.
- Government: Security baselines (and audits) don’t look kindly on end-of-life devices.
- Non-profit: Donor trust—and tight budgets—demand reducing avoidable risk.
A quick readiness check
- Do we know exactly which devices can run Windows 11—and which can’t?
- Have we budgeted for replacements and mapped a rollout schedule?
- Are line-of-business apps (EHR/SIS/claims/finance) tested on Windows 11?
- Do we have a plan for training, data backup, and rollback?
- If we must use ESUs on a few machines, is that usage tracked and time-boxed?
If your answer to “Are we ready for Windows 10 end of life?” is anything but a confident yes, it’s time to act.
We can help—without the fire drill
Our Chicago-based team works with SMBs in healthcare, education, insurance, government, and non-profit every day. We’ll:
- Audit your environment and compatibility
- Prioritize replacements and upgrades (with no surprises)
- Pilot, deploy, and train with minimal disruption
- Put guardrails in place for any short-term ESUs, then retire them on schedule
Bottom line: October 2025 is a hard deadline. The longer you wait, the tougher—and more expensive—the transition becomes.
Need a hand getting to Windows 11 the right way? Let’s talk.
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