For most IT departments, upgrading to Windows 11 is the preferred long-term strategy if hardware allows. It delivers ongoing full support, the latest security features, and no extra update fees. However, if certain PCs cannot meet requirements or you need more time, staying on Windows 10 with Extended Security Updates (ESU) can buy a temporary reprieve with critical patches.
To understand the high-level differences before diving in, check out our breakdown of Windows 10 vs. Windows 11.
Key Take-Aways
- Upgrade to Windows 11 (Modern & Future-Proof): Includes full security/feature updates and improved built-in security (TPM 2.0). Requires compatible hardware and minor user retraining.
- Stay on Windows 10 ESU (Short-Term Safety Net): No immediate hardware changes and a familiar interface. However, it involves annual costs and lacks new performance improvements.
Upgrading to Windows 11: Pros and Cons
Windows 11 is Microsoft’s latest OS, and upgrading ensures your organization runs a fully supported, up-to-date platform. For those deciding which version fits their organization, we've compared Windows 11 Pro vs. Enterprise to help you choose.
Pros of Moving to Windows 11
- Complete Security & Feature Updates: Access all regular patches and bug fixes at no extra cost. Windows 11 enforces modern protections like TPM 2.0 and Secure Boot by default.
- Avoid ESU Licensing Costs: Eliminate the need for paid ESU programs (which can cost $61+ per PC annually).
- Productivity Enhancements: Features like Snap Layouts, a revamped Start menu, and AI-powered tools help boost user efficiency. See the top Windows 11 features every IT leader should know.
- Long-Term Compliance: Stay compliant with industry standards (PCI-DSS, HIPAA) that may view Windows 10 as non-compliant after support ends.
- Performance Gains: Optimization for the latest CPUs, NPUs, and Wi-Fi 7 ensures better battery life and speed.
Cons of Moving to Windows 11
- Hardware Requirements: Older PCs (pre-2017) often lack the necessary 8th Gen Intel/AMD Zen 2 CPUs or TPM 2.0.
- UI Changes: Users may face a slight learning curve with the centered Start menu and taskbar changes.
- Compatibility Testing: Legacy in-house apps or specialized hardware may require vendor patches to run smoothly on the new OS.
Staying on Windows 10 with ESU
If upgrading isn't an option today, the Extended Security Update (ESU) program provides a temporary bridge. It is vital to understand the Windows 10 end-of-support security risks if you choose to delay.
For those moving forward with this path, review our practical guide to Windows 10 ESU enrollment and these 10 things you need to know about ESU.
Note: ESU is a strategy of delay, not advancement. It keeps systems secure but frozen in time regarding features and performance.
Conclusion and Recommendations
The choice comes down to a trade-off between short-term convenience and long-term gains. Upgrading to Windows 11 as soon as feasible is widely considered the best practice. Delaying can have major impacts on your organization if next steps aren't clearly defined.
Our Recommendation: Choose Windows 11 wherever you can. For machines that must stay on Windows 10, enroll them in ESU as a last resort, but begin planning your hardware refresh or migration immediately.
Ready to modernize your fleet? Reach out to our team today for an assessment of your hardware compatibility and a seamless transition plan.
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To summarize the trade-offs between upgrading to Windows 11 and staying on Windows 10 with ESU, the following table provides a side-by-side comparison:
| Criteria | Upgrade to Windows 11 | Stay on Windows 10 (with ESU) |
|---|---|---|
| Security Updates | Full ongoing security updates and improvements included by default (no special fees). Improved security baseline (TPM 2.0, Secure Boot, VBS) provides stronger protection out-of-the-box. | Critical security patches only, via paid ESU program. No new security features beyond what Windows 10 already has; fewer protections against modern threats long-term. |
| Cost Implications | No additional OS cost if you have Windows 10 licensing – Windows 11 is a free upgrade on supported devices. Avoids the need for yearly ESU purchase. Initial costs may come from hardware upgrades if required. | Requires purchasing ESU licenses (yearly per device cost) to get post-2025 patches. Costs increase each year, adding to IT budget. Defers hardware purchase costs for now, but those will recur when upgrade becomes unavoidable. |
| Features & Performance | Access to the latest features (enhanced UI, Snap Layouts, DirectStorage, integrated Teams/AI features, etc.) and performance optimizations that Microsoft releases for Windows 11. Continued improvements to efficiency and support for new hardware tech. | Stuck with Windows 10’s feature set as of 2025 – no new features or improvements will be added after EOL. Over time, users and IT miss out on productivity enhancements. Performance may stagnate or degrade relative to newer OS on newer hardware. |
| Hardware Requirements | Must have relatively modern hardware (must pass Windows 11 compatibility – 64-bit CPU from ~2018+ and TPM 2.0 enabled). Older PCs need component upgrades or replacement to run Win11 officially. | Runs on existing Windows 10 hardware, including older PCs that do not meet Win 11 requirements. No immediate hardware changes needed – useful for legacy or specialized machines that can’t be replaced yet. |
| User Impact | New UI/UX: generally positive reception but does require adjustment from users (centered Start menu, taskbar changes, etc.). May require user training or a short adaptation period. IT should prepare support for transition. | Familiar UI/UX: no changes for users, so no retraining needed. Users and workflows remain on the known Windows 10 interface, avoiding any disruption or learning curve. |
| Software/Device Compatibility | High compatibility in most cases (Windows 11 was designed to run Windows 10 apps), but some legacy or niche software/hardware might need updates or cannot run on Win11. Testing is needed for critical apps, and updates or replacements may be required for full compatibility. | Guaranteed compatibility with all existing applications and devices that currently work on Windows 10, since nothing in the environment changes. However, as time goes on, new software releases or devices might not support Windows 10, creating future limitations. |
| Vendor & Third-Party Support | Fully supported by Microsoft until at least 2030 (and likely beyond, with Windows 11’s lifecycle). Third-party vendors will prioritize Windows 11 for driver updates, software support, and certifications. You remain in alignment with the current technology curve. | Partial and diminishing support. Microsoft support is limited to security fixes via ESU. Third-party vendors will increasingly drop or limit support for Windows 10 versions after 2025, which could lead to compatibility issues with new software or peripherals over time. |
| Compliance & Security Posture | Strong compliance stance: Windows 11’s enhanced security features can help meet security standards and regulations. Staying current with OS updates ensures auditors see a supported, modern OS with all protections enabled. | Growing compliance risk: Running an out-of-support OS (even with ESU) may not satisfy certain regulatory requirements after a point. Lacks advanced security tech present in newer OS, potentially leaving known gaps. Need compensating controls to mitigate security risks on older OS. |
| Longevity/Future-Proofing | Long-term solution – puts you on the latest OS that will continue to be developed and supported. No hard cutoff dates imminent; you can ride the normal lifecycle and plan for the next upgrade cycle in the distant future. | Short-term stopgap – extends Windows 10 support by up to 3 years maximum. After ESU period, no further extensions; ultimately you will need to upgrade or face running unprotected OS. ESU essentially postpones the inevitable upgrade, ideally to allow time to prepare for it. |
