FAQ: Windows 10 to Windows 11 migration guide

Microsoft will sunset free support and security updates for Windows 10 on October 14, 2025. The company has put forth some basic recommendations in its Windows 11 transition guide: Back up your files, prepare your devices, and get familiar with what the new OS has to offer.

But with the clock ticking, enterprise security and IT teams have bigger tasks to tackle. They must determine soon whether remaining Windows 10 machines should (or can) be updated or upgraded now, or if it makes sense to pay for a year (or more) of extended support. 

Here are the questions every IT pro should know the answers to as the transition looms.

Q: What does “end of support” for Windows 10 mean for your organization?A: Microsoft has a standard 10-year lifecycle policy for operating systems. After Oct. 14, 2025, the company will no longer provide free security patches, software updates, bug fixes, or technical support. 

(The October 2025 deadline does not apply to devices enrolled in the Windows Enterprise long-term servicing channel (LTSC). Mainstream support for Windows 10 Enterprise LTSC 2021 devices ends on Jan. 12, 2027.)

Q: What happens if I don’t update to Windows 11 by October 14?A: Devices that continue to run the old operating system without Microsoft support will be exposed to known security threats, and some Windows 10 OS functionality may no longer be supported. Other features and functionality may also stop working over time.

Q: What are the primary risks and potential business impacts of continuing to use Windows 10 after the end-of-support date?A: Because Windows 10 will no longer receive security updates, OS flaws that will be patched on Windows 11 systems will remain as vulnerabilities on Windows 10, which makes you a target for hackers and malware.

Even if you don’t fall victim to a direct attack, you may fall out of compliance with regulations and industry standards: Windows 10 point-of-sale systems will no longer meet PCI-DSS requirements, for instance. You may also find that some software you rely on will receives update that make it no longer compatible with Windows 10.

Q: What are some of the advantages of Windows 11?A: Windows 11 officially launched in 2021 as a measure to support how the pandemic changed work, promising chip-to-cloud security and better protection for remote and hybrid professionals. Since then, the operating system’s phased rollout, along with new hardware features on Windows 11-ready PCs, have brought consumers and organizations an updated user interface, additional applications, and advanced developer tools.

Q: What are the new security features Windows 11 provides? A: Windows 11 requires security-focused hardware enhancements including use of the Trusted Platform Module (TPM) 2.0 for encrypting data and malware protection, as well as UEFI Secure Boot. Additionally, the OS allows users more control over privacy and data settings and utilizes a passwordless login option for reduced reliance on passwords. 

The system also supports VPNs and secure browsing tools. Its BitLocker feature encrypts your PC’s entire hard drive and all its data, and can also work to encrypt files on external media like USB drives. 

Advanced administrator protections have been added as well that require user authentication through Windows Hello before any administrator actions can be performed. And Windows 11 also automatically includes Microsoft Defender antivirus protection and a Smart App Control functionality that screens the trustworthiness of applications with AI before they run on the device.

At a glance: 5 key Windows 10 end-of-support facts
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The deadline is final: Free security updates, bug fixes, and technical support for Windows 10 end on October 14, 2025.
Security risks are real: Using Windows 10 after October 15 exposes your devices to unpatched vulnerabilities and makes you a target for malware and hackers.
Hardware can be a hurdle: While the Windows 11 upgrade is free for eligible devices, many older PCs won’t meet the new hardware requirements.
There’s a paid grace period: Commercial customers can opt into the Extended Security Updates (ESU) program to get one more year of Windows 10 support for $61 per device. Organizations can purchase two additional years of extended support, but fees double each year. (Consumers can get one year of extended support for free if they meet certain requirements.)
ESU is a temporary solution: Even if you opt for extended support, you still need to build a phased rollout plan well before your October 2026, 2027, or 2028 deadline.

Q: Can my hardware run Windows 11?A: While many Windows 10 computers can run Windows 11, not all can: The Windows 11 requirements include specific hardware that supports Microsoft’s aim to enhance security. The new system requirements include a recent processor, TPM 2.0, UEFI Secure Boot, and a minimum of 4GB of RAM. 

While technically Windows 11 can be installed on incompatible devices and unsupported hardware, functionality is not guaranteed. If your device is not compatible, the safest route is to replace it with a new PC with the updated operating system already installed, or to upgrade individual hardware components as needed.

Q: What will it cost to upgrade to Windows 11? How can I determine if I qualify for a free upgrade?A: Windows 11 is free to install on supported devices that meet the system requirements. Most Windows PC users eligible for direct upgrades to the new operating system have already received notifications; but you can check for eligibility by navigating to Settings > Update & security, then selecting Windows Update and Check for updates. You can also use Microsoft’s PC Health Check app.

Q: We have a large number of devices that don’t meet the Windows 11 hardware requirements. What should we do with them?A: As noted, it is not recommended that you install Windows 11 on unsupported devices. The registry can bypass compatibility checks and produce a working install of the OS, but the device may run more slowly than normal due to compatibility issues and will be left open to security vulnerabilities. Organizations considering doing this should run a cost-benefit analysis to determine the potential risks of unsupported methods vs. the costs of upgrading hardware. 

It’s also possible, and more secure, to upgrade device hardware components like the TPM module or processor to meet Windows 11 requirements. This too would involve a cost-benefit analysis, as it may ultimately be cheaper to simply buy new Windows 11-compatible PCs rather than spending time upgrading old ones. 

If your organization needs more time to make a decision, consider enrolling in Microsoft’s Extended Security Updates program. 

Q: What is the Extended Security Updates (ESU) program and how I do enroll? Is it a viable long-term solution for our business?A: Microsoft’s Extended Security Updates program will provide security updates and support to devices running Windows 10 beyond the October 14 deadline.

Commercial customers can purchase extended support for Windows 10 devices in one-year increments for up to three years, but the fees double each year, from $61 per device for the first year to $122 per device the second year and $244 per device the third year. After an organization’s ESU period has ended, support will be discontinued and devices running Windows 10 will be at risk for vulnerabilities.

For the first time, Microsoft is offering its ESU program to consumers, for one year only. Individuals who sign up for extended support can do so for free if they use Windows Backup to sync their PC’s settings, or they can pay Microsoft $30 or redeem 1,000 Microsoft Rewards points. You’ll find step-by-step instructions on how to sign up here.

Q: How can we manage the migration process smoothly across our organization?A: Although time is tight, you can still do an audit of the devices across your enterprise that are running Windows 10 before the October 14 deadline. Such an audit can determine which devices are eligible for Windows 11 updates and which will need hardware upgrades for compatibility with the new operating system, or will need to receive extended support or be replaced.

An important part of that audit is determining what legacy software is running your Windows 10 devices — and whether that software can run on Windows 11, be updated to do so, or be replaced with a more modern application.

From there, outline a rollout approach. Consult with C-suite leadership, security, and IT professionals on a timeline and best practices to communicate the changes to employees. Make sure files are backed up and other security systems are up to date before the launch. 

Q: What is the role of our IT team versus our C-suite and security leadership in this transition?A: If you haven’t upgraded to Windows 11, you’ll most likely need C-suite buy-in for your Windows 11 transition, as leadership will need to approve resource allocation and budget across the organization and lead rollout communication, stakeholder updates, and change management. You’ll also need C-level approval to opt in to Microsoft’s ESU program. 

IT leaders should work alongside security teams to assess any existing vulnerabilities and patch them before the transition. The IT team should also lead technical aspects of the migration, audits, hardware and software compatibility assessments, and training for employees as the rollout happens. 

Security professionals should ensure compliance and data protection, and should educate employees around best practices with Windows 11’s new security features. 

If your organization relies on Windows, don’t let the short time frame paralyze you. Get started now for the transition to Windows 11: you’ll never regret being prepared.