We’re just over a month away. If you still have Windows 10 in your business, the planning window has gone. It’s time to move.

After 14 October 2025, Microsoft stops security updates and bug fixes for Windows 10. You can keep using it, but you’ll be running unprotected software that attackers target. Many vendors and some insurers also expect supported systems, so expect friction during audits or incidents.

What to do this week (days 0–7)

1) Name an owner today
Give one person the authority to make decisions and unblock issues.

2) Get a clean device list
Every PC: user, role, CPU, RAM, storage, age/warranty.

3) Sort devices into three categories (Crosstek uses these for clarity)

  • Ready for Windows 11 (Capable of upgrade)
    Meets requirements and will run well after upgrade.

  • Technically upgradable but not recommended
    Meets the bare minimum but will feel slow or unstable after upgrade (older processors, low memory, or slow storage). We flag these so you don’t upgrade into poor performance.

  • Not capable
    Fails Windows 11 requirements (e.g., no TPM 2.0 or unsupported CPU). Replace or isolate.

4) Decide on ESU (Extended Security Updates)
Paid updates for Windows 10. Costs rise each year. Use only as a short bridge while you finish the rollout.

5) Pilot + backup
Pick 5–10 users, test your core apps, and confirm you can restore files before upgrading anyone else.

6) Roll out in waves
Prioritise finance, privileged users, and frontline teams. Track blockers daily.

How Crosstek helps you move quickly (with minimal disruption)

Rapid audit

  • Pull a live inventory from your estate (or build one fast if none exists).

  • Mark each device as Capable, Not recommended, or Not capable with a simple report your leadership team can act on.

Clear, short plan

  • A two–four week schedule with who moves when, outside busy periods.

  • ESU coverage where needed, with end dates so it doesn’t drift.

Right upgrades, first time

  • For Capable devices: upgrade to Windows 11 with standard build, policies, and checks.

  • For Not recommended: we explain the performance risk in plain terms and propose options (RAM/SSD uplift where it makes sense, or replace).

  • For Not capable: like-for-like modern replacements, imaged and ready. We can stage data and profiles so users pick up where they left off.

Controls while you finish

  • MFA everywhere, remove local admin, tighten web/email filtering, keep third-party apps patched, and segment any remaining Windows 10 machines.

Backups and recovery

  • Confirm OneDrive/SharePoint sync or your backup jobs are working. Test restores before each wave.

Communication and support

  • Short user comms, a “What’s new in Windows 11” guide, and floor-walking/remote support on go-live days.

Why “technically upgradable” can still be a bad call

Some Windows 10 machines meet the minimum spec but will slow people down after upgrading. Common signs:

  • 4–8 GB RAM with heavy apps or multiple browser tabs.

  • Older CPUs that struggle with modern security features.

  • Spinning hard drives instead of SSDs.

We label these Not recommended to avoid pushing a sluggish device into Windows 11 and calling it done. That usually costs more in lost time and extra support.

Quick tip: “Am I on Windows 10?”

Fast visual clue

  • Windows 10: Start button is square and usually sits left on the taskbar.

  • Windows 11: Start button is centred by default and windows have more rounded corners.
    (Note: icons can be moved left in Windows 11, so this is a clue, not proof.)

Definitive check (takes 10 seconds)

  1. Press Windows key + R.

  2. Type winver and press Enter.

  3. If it says Windows 10, you need a plan now.
    —or—
    Go to Settings > System > About to see the edition and version.

If you won’t finish by 14 October

Use ESU short-term and harden your environment while you complete the rollout:

  • Remove local admin rights.

  • Turn on MFA everywhere.

  • Tighten web filtering and email security.

  • Patch all third-party software.

  • Segment remaining Windows 10 devices and limit their access.

  • Keep verified backups and test restores.

Bottom line

There’s no runway left. A clear owner, a short pilot, and fast waves will get you over the date. ESU can buy limited time, but Windows 11 is the end state. For some devices, “can upgrade” doesn’t mean “should”—we’ll call that out so you don’t pay in performance later.

Need help with the audit, a rapid rollout plan, or short-term containment while you finish? Contact Crosstek to sort your Windows 11 move, and to review business continuity, backup, and IT support.