Series: No-Drama IT September: Last Call Before Windows 10 Sunset — Part 1 of 4.
Next week: a cyber hygiene checklist Oregon teams will actually follow.
Microsoft stops free security updates for Windows 10 on October 14, 2025. Your PCs won’t shut off, but the risk goes up and software starts to drift. Here’s what Oregon SMBs should do in the next 30 days to stay secure and productive.
10D Tech has guided Oregon teams through Windows 11 migrations with minimal disruption, and this is the 30-day plan we recommend.
What changes on October 14, 2025
Windows 10 will keep running, but Microsoft will stop releasing free security patches and technical support. That gap creates an easier target for malware, ransomware, and data theft.
After support ends, more apps will focus on Windows 11. Compatibility issues grow, and compliance audits get tougher, especially for credit unions and financial firms in Portland, Salem, Bend and Eugene.
Why this matters for business leaders
Security risks climb fast
Unpatched systems become easy targets. One compromised device can move across your network and hit file shares, email, and backups.
Software and hardware drift
Vendors tune features for the latest OS. Older drivers and apps can stall, crash, or lose support, dragging down your team and customer experience.
Compliance and audit headaches
Regulated Oregon organizations face higher scrutiny. Running unsupported operating systems can lead to findings and costly remediation.
Your options (pick a path, then move)
- Upgrade compatible PCs to Windows 11.
- Replace incompatible hardware with modern devices.
- Buy time with Extended Security Updates (ESU) for a limited period.
- Switch to Linux on select roles (often for kiosks or dedicated tasks).
Important: make a verified backup first. Image critical machines and save files to the cloud or offsite storage so nothing is lost in the shuffle.
Extended Security Updates: a short runway, not a destination
ESU adds paid security patches for Windows 10 for a limited term after EoS. Register before the deadline to stay eligible. Some devices may qualify via Windows Backup syncing to OneDrive; others will require a per-device fee.
Use ESU as a bridge plan for critical workstations, then complete your migrations. Stretching ESU too long just pushes risk (and costs) into next quarter.
A 30-day plan for Oregon SMBs
Week 1: inventory and backup
List all Windows 10 devices, age, CPU, RAM, storage, and critical apps. Run a compatibility check for Windows 11. Back up user data and system images, then test a restore.
Week 2: decide per device
Group machines into upgrade, replace, ESU-bridge, or retire. Map app dependencies, printers, and domain joins so cutovers are clean.
Week 3: pilot and train
Upgrade a small group in Portland and Eugene offices. Validate line-of-business apps, VPN, and printers. Share a short Windows 11 “what changed” guide with screenshots.
Week 4: migrate and stabilize
Roll out by team, after hours if needed. Keep help desk coverage ready for the first 48 hours and schedule a follow-up to tidy loose ends.
Local story: Alex keeps a Portland credit union quiet and calm
10D Tech supports Alex and his “Tumble Weeds Are Us”, fictional consulting firm. He also volunteers on a Portland credit union board. Their branch PCs were split; half were upgrade-ready, and the other half were too old. The team wanted to wait, but the audit clock was ticking.
Alex built a plan with 10D Tech and pushed for an inventory first, then a pilot in the downtown branch. The pilot caught a teller app that needed a patch and a USB check scanner driver that misbehaved.
They put five PCs on ESU for a quarter, ordered new compliant hardware for those roles, and migrated everyone else to Windows 11 over two evenings.
Result: no downtime, no surprise fees, and a smoother audit. The only complaint was new taskbar muscle memory; fixed with a quick lunch-and-learn and coffee.
Need a hand or a second opinion?
Planning a migration? Our Cloud solutions & migrations team can map your rollout and keep users moving. For budgeting and roadmap questions, lean on IT assessments & strategy consulting.
Mini-CTA: Want a quick sanity check on your upgrade path? Call (541) 243-4103 or (971) 915-9103, or book at 10dtech.com/discoverycall.
If you hit a snag mid-migration, our Emergency IT support & incident response crew can jump in fast; after hours and weekends available.
What works? Want a pilot that doesn’t derail your week? Set a time for a 15-minute consult at 10dtech.com/discoverycall.
FAQs
Q1: What happens if we do nothing after Windows 10 EoS?
A: PCs keep running, but you stop getting free security patches. Risk climbs, software support fades, and audits get harder.
Q2: How do we know which PCs can run Windows 11?
A: Check CPU, TPM 2.0, RAM, and storage. Your IT team can run a compatibility tool and sort devices into upgrade or replace buckets.
Q3: Is ESU worth it for Windows 10?
A: Yes as a short bridge for critical roles. It buys time but shouldn’t replace a migration plan.
Q4: Can we move a few workloads to the cloud during this shift?
A: Yes—email, files, and apps often move during OS upgrades. Our Cloud solutions & migrations team can help.
Q5: Will compliance auditors ding us for Windows 10?
A: Unsupported systems often show up in findings. A documented plan and timeline helps, but upgrades close the gap best.
Ready to lock in your Windows 11 plan without drama? Call (541) 243-4103 or (971) 915-9103, or book your Free IT Checkup at 10dtech.com/discoverycall.
