Windows 10 ESU Year 2: What It Costs Your Business and What to Do Next
By TechTrone Team — Published 2026-11-07
Quick answer: Windows 10 reached end of support on October 14, 2025. Businesses that still run it can only stay protected through Microsoft's paid Extended Security Updates (ESU) program. ESU Year 2 began on October 14, 2026 and costs $122 per device, double the Year 1 price, and businesses that skipped Year 1 must pay for it too, bringing the catch-up cost to $183 per device. For most offices, that money is better spent moving to Windows 11.
If your business still has Windows 10 PCs at the front desk, in the back office, or running a piece of legacy software, this guide explains what ESU Year 2 really costs, the risks of doing nothing, and a practical plan for getting every machine onto a supported operating system.
What This Guide Covers
- 1. Where Windows 10 stands in late 2026
- 2. What ESU Year 2 costs your business
- 3. What ESU does and does not cover
- 4. The real risks of running unsupported Windows 10
- 5. ESU vs. upgrading vs. replacing: how to decide
- 6. A step-by-step Windows 11 migration plan
- 7. Frequently asked questions
1. Where Windows 10 Stands in Late 2026
Microsoft ended mainstream support for Windows 10 on October 14, 2025. Since then, Windows 10 PCs no longer receive free security patches, feature updates, or technical support. The operating system still boots and runs, which is why many businesses have not noticed a problem yet. But every month, newly discovered vulnerabilities go unpatched on any machine that is not enrolled in ESU.
For businesses, Microsoft offers ESU for up to three years, through October 2028. Each year is priced separately, and the price doubles every year to push organizations toward upgrading.
2. What Does Windows 10 ESU Year 2 Cost?
Here is how commercial ESU pricing breaks down per device:
| ESU Period | Coverage Dates | Price per Device |
|---|---|---|
| Year 1 | Oct 2025 – Oct 2026 | $61 |
| Year 2 | Oct 14, 2026 – Oct 2027 | $122 |
| Year 3 | Oct 2027 – Oct 2028 | Expected to double again |
The Catch-Up Rule
ESU is cumulative. Security updates build on each other, so Microsoft requires you to purchase any years you missed. A business that skipped Year 1 and enrolls now pays $61 + $122 = $183 per device just to get current.
What That Means for a Typical Office
- 10 Windows 10 PCs enrolling late: about $1,830 for one year of patches
- 25 Windows 10 PCs enrolling late: about $4,575
- Through Year 3, the cumulative per-device cost can approach the price of a new business-class computer
That is money spent on a machine that still has to be replaced eventually. Unless you have a hard technical reason to stay on Windows 10, ESU is a bridge, not a destination.
Note: Licensing details and pricing can vary by purchase channel and agreement. Confirm current pricing with your IT provider or Microsoft licensing partner before you buy.
3. What ESU Does and Does Not Cover
ESU Includes
- Critical and important security updates for Windows 10, version 22H2
- Continued eligibility for monthly security patches through the coverage year
ESU Does Not Include
- New features or design changes
- Non-security bug fixes
- General technical support from Microsoft
- Any guarantee that third-party software vendors will keep supporting Windows 10
That last point is important. Browsers, accounting packages, EHR systems, and security tools are steadily dropping Windows 10 support. Even a fully patched Windows 10 PC can end up running unsupported applications.
4. The Real Risks of Running Unsupported Windows 10
- Ransomware and malware. Attackers actively target known, unpatched Windows vulnerabilities. One unprotected PC can be the entry point to your whole network. Learn more about the cybersecurity threats businesses face in 2026.
- Compliance failures. HIPAA, the FTC Safeguards Rule, PCI DSS, and most client security questionnaires expect supported, patched systems. Unsupported operating systems are a common audit finding.
- Cyber insurance problems. Many insurers ask whether you run end-of-life software. A "yes," or an inaccurate "no," can affect your premium or a future claim.
- Software compatibility. As vendors drop Windows 10, you may lose access to updates for critical business applications.
- Hidden productivity costs. Older machines that cannot run Windows 11 are usually slow, and slow PCs cost staff time every day.
5. ESU vs. Upgrade vs. Replace: How to Decide
Every Windows 10 device in your business falls into one of three buckets.
Bucket 1: Upgrade in Place to Windows 11
If the PC meets Windows 11 requirements (a supported processor, TPM 2.0, Secure Boot, 4 GB+ RAM, and 64 GB+ storage), the upgrade is free. For business-class machines from roughly 2019 onward, this is often the fastest and cheapest path.
Bucket 2: Replace the Hardware
If the PC cannot run Windows 11, or it is more than five years old, replacement is usually the smarter investment. Paying $183 or more in ESU on a machine that is already near the end of its life rarely makes financial sense. Our computer buying guide covers what to look for in a business PC.
Bucket 3: Enroll in ESU (Temporarily)
ESU is the right choice only when a device must stay on Windows 10 for a defined period, for example:
- It runs specialized software or controls equipment (imaging, lab, or manufacturing systems) that is not yet certified for Windows 11
- Replacement hardware is budgeted for a specific upcoming quarter
- You need a few extra months to complete a phased migration
Even then, isolate those machines on their own network segment, limit internet access, and protect them with managed endpoint protection.
6. A Step-by-Step Windows 11 Migration Plan for Businesses
- Inventory every device. Record the OS version, hardware model, age, and Windows 11 eligibility. A managed IT provider can pull this automatically from monitoring tools.
- Test critical applications. Confirm that your accounting, practice management, EHR, CAD, and line-of-business apps are supported on Windows 11.
- Sort devices into upgrade, replace, or ESU buckets. Set a target date for each.
- Back up user data. Make sure files are in OneDrive, SharePoint, or a tested backup before anything is touched. See why data backup matters.
- Upgrade in waves. Start with a pilot group, fix any issues, then roll out to the rest of the office after hours to avoid downtime.
- Harden the new setup. Turn on BitLocker encryption, enforce MFA, and apply security baselines through Microsoft 365 and Intune management.
- Retire old hardware securely. Wipe or destroy drives before recycling or donating PCs.
- Keep patching. Windows 11 also needs ongoing patch management to stay secure.
Pro tip: Bundle the migration with a hardware refresh plan. Replacing PCs on a predictable four-to-five-year cycle avoids the next end-of-life scramble.
Frequently Asked Questions
Is Windows 10 still safe to use in 2026?
Only if the device is enrolled in Extended Security Updates and well protected. Without ESU, Windows 10 no longer receives security patches and becomes more vulnerable every month.
How much is Windows 10 ESU Year 2 for businesses?
Year 2 costs $122 per device. Businesses that did not buy Year 1 must also pay for it, for a total of $183 per device.
Can I skip ESU Year 1 and only buy Year 2?
No. ESU is cumulative, so you must purchase any missed years to enroll.
How long can businesses get Windows 10 ESU?
Commercial ESU is available for up to three years after end of support, through October 2028.
Is upgrading to Windows 11 free?
Yes, for eligible Windows 10 devices with valid licenses. The real costs are planning, testing, labor, and replacing hardware that does not meet requirements.
Get Your Windows 10 Devices Off the Risk List
TechTrone helps Long Island and New York businesses inventory devices, plan budgets, and complete Windows 11 upgrades with minimal downtime. Whether you need a one-time migration project or ongoing managed IT services, we can help. Contact us for a free Windows 10 readiness review.