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Still Using Windows 10? Check Your Business ESU and Migration Plan

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Brandon Phipps

Windows 10 business computer beside a migration checklist and modern laptop

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A Windows 10 computer may still handle your invoices or run a program the business relies on. Before keeping it in service for another year, ask IT to document its support status and a workable migration date. A device-by-device review helps you budget for the change without losing track of the work that depends on an older PC.

What should a business still using Windows 10 check?

Record the exact Windows edition and version, confirm the applicable support or Extended Security Updates (ESU) arrangement, and have IT verify update installation. Then assess Windows 11 compatibility, application support, backup recovery, and the cutover schedule. Give every remaining device a named owner and a decision date.

Check the coverage period on each device

For Windows 10 releases that reached end of support on October 14, 2025, ordinary support has ended. Microsoft's commercial ESU schedule lists Year 1 ending October 13, 2026, Year 2 ending October 12, 2027, and Year 3 ending October 10, 2028. As of November 4, 2026, a Year 1 purchase alone leaves the current coverage question unresolved.

Ask the administrator to identify the exact edition, licensing route, and applicable coverage year. Long-Term Servicing editions have their own lifecycle details, which should be checked against the precise product. Keep the evidence in the device record so the next review can start from a confirmed position.

What does commercial ESU cover?

Microsoft's Windows 10 ESU program supplies critical and important security updates to enrolled, eligible PCs. Its standard prerequisites include version 22H2. New features and general operating-system support fall outside that coverage. Commercial enrollment also has annual purchase rules, including earlier-year requirements when joining later.

Have your licensing provider confirm the terms for your organization. Keep the software charge separate from enrollment labor, ongoing maintenance, and migration work in the quote. The consumer enrollment offer has separate eligibility rules; the administrator should establish which program fits the business device.

Request evidence of activation and the latest applicable installed security update. A purchase receipt establishes a licensing transaction. The device's update record helps IT confirm the result. Our business IT quote checklist can help you assign those responsibilities.

What does commercial Windows 10 ESU cost in 2026?

Microsoft lists standard commercial ESU pricing at $61 per device in Year 1 and says the price doubles each year. That puts the standard per-device prices at $122 in Year 2 and $244 in Year 3. These are planning figures based on Microsoft's published pricing model; ask your licensing provider to verify the actual quote and any applicable exceptions.

Standard commercial ESU planning costs per device
Coverage yearAnnual priceCumulative total
Year 1 (ended October 13, 2026)$61$61
Year 2 (through October 12, 2027)$122$183
Year 3 (through October 10, 2028)$244$427

Since Year 2 is now underway, a business joining the commercial program for the first time generally must pay for both Year 1 and Year 2. Partial-year purchases aren't offered. For ten devices newly enrolled in Year 2, the standard cumulative license amount would be $1,830 before enrollment labor or other charges. Compare that amount with the cost of upgrading or replacing those computers rather than treating ESU as an open-ended expense.

Ask IT to follow Microsoft's current commercial enrollment prerequisites, then verify activation and the latest applicable security update. Preparation updates alone do not establish that a device is enrolled.

Build an inventory around the work people do

Include rarely used computers and spare devices. Ask the person who uses each one to identify the business task it supports and what would happen if that task stopped during a migration.

  • Record the device name, assigned user, Windows edition and version, hardware model, and location.
  • List critical applications with their versions, license owners, installation sources, and vendor contacts.
  • Identify local files, shared folders, printers, scanners, and other attached equipment.
  • Note the business calendar, including payroll, billing runs, and other periods when a change would cause disruption.

Store credentials in the approved password system. The worksheet should identify the person responsible for access without containing passwords or recovery secrets.

Will the PC and its applications support Windows 11?

Microsoft's compatibility guidance covers requirements including a supported processor, TPM 2.0, and Secure Boot capability. Use PC Health Check where applicable and consult the computer manufacturer. Application requirements can exceed the operating system's minimum specifications.

Ask each critical software vendor about the exact version in use, any required upgrade, supported peripherals, and license transfer. Record the answer or support document. A generic statement that a product supports Windows 11 may leave an older application release or a specialist scanner unaddressed.

For hardware decisions, compare the proposed work with the computer's condition and expected service life. Our repair, upgrade, or replace guide provides a starting point for that conversation.

Use a migration decision worksheet

Complete one record for each remaining Windows 10 device
DecisionEvidence to recordPerson responsible
Current support statusEdition, version, applicable lifecycle or ESU term, activation and update checksIT administrator
Upgrade suitabilityHardware assessment and application-vendor answersIT with application owner
Business continuityVerified data locations, recovery check, approved fallbackIT and business approver
Chosen routeUpgrade, replace, retire, or time-limited exception with reasonBusiness owner
Cutover acceptanceUser task, expected result, actual result, unresolved itemsPerson who uses the device
Next actionApproved budget, target date, owner, next reviewNamed project owner

Use “awaiting vendor answer” or another clear status when evidence is missing. Assign a follow-up date so the machine stays visible in the plan.

Test a pilot before moving the remaining devices

Select a representative computer and agree on acceptance tasks with its user. Choose work that exercises the actual business dependency, such as producing an approved report or scanning a test document into the correct application. Use authorized test data and record each result.

Before the cutover, confirm the backup and the recovery procedure for records affected by the change. Agree on the conditions that would pause the migration and who can authorize the next step. Our guide to testing business recovery explains how to check whether work can resume.

After acceptance, update the inventory and the support record. Retain or erase the old device according to the business's approved data-retention and equipment-disposal process.

Windows 10 business migration FAQs

Will the computer stop working because support ended?

Microsoft says Windows 10 PCs can continue operating. Review update coverage and the applications the business relies on before deciding how long to keep one in use.

Does buying ESU finish the migration plan?

Set a migration or retirement date alongside the temporary coverage decision. Track vendor dependencies and the person responsible for resolving them.

Should we replace every Windows 10 PC immediately?

Assess each device. Hardware suitability, software requirements, condition, and the cost of disruption should inform the approved route and timing.

What should we bring to an IT assessment?

Bring the device list, application versions, vendor contacts, known problems, current coverage evidence, and dates when business work cannot be interrupted.

Plan your next step with Second Star Technologies

Second Star Technologies helps Bakersfield and Kern County businesses discuss computer support and migration needs. Review our managed IT services or request an assessment with your device list. Ask for a scope that identifies assessment work, licensing, backups, testing, and responsibilities.

Read the audio summary transcript

An older office computer can still open the accounting program and print an invoice. That tells you the work runs today. To plan its future, you also need to know which Windows edition it uses, what security coverage applies, and how you'll move the work when the time comes.

Welcome to The IT Edge: Business Tech Made Simple, from Second Star Technologies. Today we're looking at business computers that still run Windows 10 and the decisions an owner should put in writing.

Start with your device list. Include the spare laptop, the front desk computer, and the workstation used for one job each month. Give each device an owner. Record its Windows edition and version, the programs people depend on, and any attached equipment. Your payroll computer may need a different change window from a spare office laptop.

Ask your administrator to confirm the support path for each device. Windows editions can have different lifecycle rules, so the product name alone leaves questions unanswered. For a business PC using commercial Extended Security Updates, ask which coverage year applies and how the administrator verified that the computer can receive the applicable updates. Keep that evidence with the device record.

Extended Security Updates provides specified security fixes for eligible, enrolled machines. It doesn't make an aging computer a permanent solution. Have your licensing provider explain the current terms and any earlier-year purchase requirements. Separate the software charge from the work to enroll and maintain the computer, so you can compare the full cost with migration or replacement.

Next, check the route to Windows 11. Use Microsoft's compatibility guidance and the computer manufacturer's information. Then contact the vendors behind your critical software. Ask about the exact program version you use, any required upgrade, supported peripherals, and how the license moves.

A computer can meet the operating system requirements while still needing an application update or a different scanner driver. Put those dependencies in the plan before scheduling the change.

Choose a small pilot before moving the remaining computers. Have a person who normally uses the system complete a business task with approved test data. They might produce a report, open a business file, or scan a document into the correct application. Record the expected result, what actually happened, and who will resolve any problems.

Plan the cutover around your business calendar. Before changes begin, confirm where records are stored, who has approved access, and how you'll restore affected data if something fails. Agree on a point at which the technician pauses and contacts the business owner. Keep the old equipment under the approved security and retention plan until the replacement has passed its checks.

Each remaining Windows 10 computer needs a decision and a date. Some can move after a successful pilot. A machine with unsuitable hardware may need replacement. A computer tied to specialist software may require a temporary exception while the vendor helps establish a workable exit plan.

For a Bakersfield or Kern County business, bring your device list and application requirements to Second Star Technologies. We can discuss the assessment, backup checks, licensing questions, and migration work to include in your support scope. Use the article's worksheet to record the evidence, the person responsible, and the next review date.

References

Microsoft. (n.d.). Extended Security Updates (ESU) program for Windows 10. Microsoft Learn. Program coverage and prerequisites.

Microsoft. (n.d.). Lifecycle FAQ: Extended Security Updates. Microsoft Learn. Coverage periods and licensing rules.

Microsoft. (n.d.). Windows 11 specifications and system requirements. Compatibility requirements.

Sources reviewed November 6, 2026. Confirm the exact product lifecycle and current licensing terms for each device before making changes. Written by Brandon Phipps, owner of Second Star Technologies.

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