Windows 10 Is Dead: What Grants Pass Small Businesses Need to Do Before Microsoft 365 Freezes This Summer

If your Grants Pass business is still running Windows 10, the clock is ticking. Microsoft officially ended support for Windows 10 on October 14, 2025, and Microsoft 365 will stop rolling out new features to Windows 10 PCs starting this summer. Your computers will keep turning on, but the safety net is quietly being pulled out from under them. Here is a straight-forward plan to get your office ready without panic and without over-spending.

What actually changed on October 14, 2025

Microsoft stopped shipping security patches, bug fixes, and technical support for Windows 10. That does not mean your PCs stopped working — it means every new vulnerability discovered from that day forward will never be patched on Windows 10. Attackers know this. Unpatched operating systems become known-good targets for ransomware and credential theft within weeks.

For a Grants Pass small business, that matters for three reasons:

1. Cyber insurance. Most Oregon cyber-liability policies now require that all business endpoints run a supported operating system. An unpatched Windows 10 machine can be grounds for a denied claim.
2. Industry compliance. HIPAA, PCI-DSS, and most vendor-security questionnaires explicitly require supported operating systems.
3. Microsoft 365 is next. If you use Outlook, Word, Excel, or Teams, read the next section carefully.

The Microsoft 365 freeze: three dates to know

Microsoft has announced that Microsoft 365 Apps running on Windows 10 will stop receiving new features on a staggered timeline, based on which update channel your business uses:

• Current Channel (most home and small-business subscriptions): August 2026
• Monthly Enterprise Channel: October 13, 2026
• Semi-Annual Enterprise Channel: January 12, 2027

After those dates, your Office apps on Windows 10 will still open and still work, but new features — including new security and phishing-protection features — stop arriving. Microsoft will continue pushing security-only updates for Microsoft 365 on Windows 10 through October 10, 2028, and then it is fully frozen.

Translation: you have roughly four months before most Grants Pass businesses start falling behind on Microsoft 365 features, and about two and a half years before the door closes entirely.

Your options, in plain English

Option 1 — Upgrade the PC to Windows 11 (cheapest). If the machine meets the hardware requirements (roughly 2018-and-newer, with TPM 2.0), a free in-place upgrade gets you back on a supported OS with no new hardware. The upgrade takes about an hour per PC and preserves your files and installed software.

Option 2 — Replace the PC (when hardware is too old). Pre-2018 hardware often cannot run Windows 11. If you are going to replace anyway in the next 18 months, do it now and skip the gap. Business-grade laptops in the $900 to $1,400 range will easily last five to seven years.

Option 3 — Enroll in Extended Security Updates, ESU (stopgap only). Microsoft offers paid ESU for Windows 10 at $61 per device for year one, doubling in year two and again in year three. For a ten-PC office, that is $610 for one extra year. Worth it only if replacement is already scheduled and you need a few months of runway.

What we don’t recommend: ignoring it. We have already seen small businesses in Southern Oregon hit by ransomware that exploited unpatched systems. Recovery costs average over a million dollars, and most small businesses that get hit never fully recover.

A realistic plan for a Grants Pass office

If you have not started yet, here is what the next 90 days should look like:

1. Inventory. Walk the office and list every PC, its age, and its OS version. A five-minute job for a 10-person office.
2. Triage. Separate the list into three buckets: Windows 11 already, Windows 10 that can upgrade in place, and Windows 10 that needs replacing.
3. Upgrade the easy ones first. Run the free Windows 11 upgrade on machines that qualify. Do it after hours and back up first.
4. Budget the replacements. Get quotes for new hardware, aim to stagger the purchases so you are not absorbing a five-PC bill in one month.
5. Update your cyber-insurance disclosure. Once you are fully on Windows 11, tell your insurance agent. Some carriers will lower premiums.

Most small businesses can finish the whole project in 60 to 90 days working with a managed IT provider. On your own, expect it to take longer and cost more per machine.

How we help

ITs Managed has been upgrading Southern Oregon small businesses through Windows 2000, XP, 7, 8, and now 10 transitions since 1989. We run the inventory, handle the upgrades after hours so your team is not interrupted, and recycle old hardware responsibly. Our clients in Jackson and Josephine counties get a flat-rate project quote up front — no surprise invoices.

If your Grants Pass or Medford business is not yet on Windows 11, schedule a no-obligation consultation and we will map out the cheapest path to a supported setup before the Microsoft 365 freeze arrives.