The Windows 10 Deadline Is Here—Are You Ready for What Happens Next?
Shawn Akins • October 13, 2025
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The clock is ticking: Learn your options for Windows 11 migration, Extended Security Updates, and cost‑smart strategies before support ends.
TL;DR
- Windows 10 reaches end of support on October 14, 2025. No more free security or feature updates after that date.
- Your three main options:
- Upgrade to Windows 11 on eligible hardware,
- Purchase Extended Security Updates (ESU) for Windows 10, or
- Refresh hardware or move to cloud desktops.
- ESU pricing starts at $61 per device for Year 1 and doubles each year for up to three years. ESU provides security fixes only—no new features or general support.
What “End of Support” Means (and Why It Matters)
On October 14, 2025, Microsoft stops releasing free monthly updates for Windows 10. That includes the security patches that protect against new vulnerabilities. After that date, devices will still run, but they’ll become increasingly vulnerable and may fall out of compliance with frameworks like HIPAA, PCI DSS, and ISO 27001.
| Path | When to choose it | What you get | Key caveats |
|---|---|---|---|
| Upgrade to Windows 11 | Most devices meet CPU/TPM 2.0 requirements and apps are compatible | Modern security baseline, long support runway, new features | Hardware eligibility, app testing, user training |
| Extended Security Updates (ESU) | You need more time for app remediation or hardware budgets | Security patches for up to three additional years | Security fixes only, price doubles each year, requires Windows 10 22H2 |
| Hardware refresh | Devices are 4–6+ years old or unsupported | Better performance, security, and energy efficiency | Capex or leasing costs, deployment planning |
| Virtualization/Cloud PC | BYOD, contractors, or legacy apps | Secure Windows 11 experience from any device | Requires identity, networking, and cost governance |
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October 20, 2025 — Early today, Amazon Web Services experienced a major incident centered in its US‑EAST‑1 (N. Virginia) region. AWS reports the event began around 12:11 a.m. PT and tied back to DNS resolution affecting DynamoDB , with mitigation within a couple of hours and recovery continuing thereafter. As the outage rippled, popular services like Snapchat, Venmo, Ring, Roblox, Fortnite , and even some Amazon properties saw disruptions before recovering. If your apps or data are anchored to a single cloud, a morning like this can turn into a help‑desk fire drill. A multi‑cloud or cloud‑smart approach helps you ride through these moments with minimal end‑user impact. What happened (and why it matters) Single‑region fragility: US‑EAST‑1 is massive—and when it sneezes, the internet catches a cold. Incidents here have a history of wide blast radius. Shared dependencies: DNS issues to core services (like DynamoDB endpoints) can cascade across workloads that never directly “touch” that service. Multi‑cloud: practical resilience, not buzzwords For mid‑sized orgs, schools, and local government, multi‑cloud doesn’t have to mean “every app in every cloud.” It means thoughtful redundancy where it counts : Multi‑region or multi‑provider failover for critical apps Run active/standby across AWS and Azure (or another provider), or at least across two AWS regions with automated failover. Start with citizen‑facing portals, SIS/LMS access, emergency comms, and payment gateways. Portable platforms Use Kubernetes and containers, keep state externalized, and standardize infra with Terraform/Ansible so you can redeploy fast when a region (or a provider) wobbles. (Today’s DNS hiccup is exactly the kind of scenario this protects against.) Resilient data layers Replicate data asynchronously across clouds/regions; choose databases with cross‑region failover and test RPO/RTO quarterly. If you rely on a managed database tied to one region, design an escape hatch. Traffic and identity that float Use global traffic managers/DNS to shift users automatically; keep identity (MFA/SSO) highly available and not hard‑wired to a single provider’s control plane. Run the playbook Document health checks, automated cutover, and comms templates. Then practice —tabletops and live failovers. Many services today recovered within hours, but only teams with rehearsed playbooks avoided user‑visible downtime. The bottom line Cloud concentration risk is real. Outages will happen—what matters is whether your constituents, students, and staff feel it. A pragmatic multi‑cloud stance limits the blast radius and keeps your mission‑critical services online when one provider has a bad day. Need a resilience check? Akins IT can help you prioritize which systems should be multi‑cloud, design the right level of redundancy, and validate your failover plan—without overspending. Let’s start with a quick, 30‑minute review of your most critical services and RPO/RTO targets. (No slideware, just actionable next steps.)
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