Windows Server 2016 and Windows 10 LTSB 2016 End of Support: Migration Strategies and ESU Options

Microsoft has announced concrete end-of-support timelines for three legacy products: Windows 10 Enterprise LTSB 2016 (October 13, 2026), Windows 10 IoT Enterprise LTSB 2016 (October 13, 2026), and Windows Server 2016 (January 12, 2027). Organizations maintaining these systems face critical decisions between migration and temporary security coverage through Extended Security Updates (ESU).

End of Support Implications

After the specified dates, these products will cease receiving:

• Security updates
• Non-security updates
• Bug fixes
• Technical support
• Online technical content updates

This creates significant vulnerability exposure, particularly for regulated industries requiring compliance with security frameworks. The ESU program serves as a stopgap solution, providing critical and important security patches for up to three additional years.

Extended Security Updates: Strategic Considerations

ESU has specific limitations enterprises must understand:

ESU Coverage	Not Included
Critical security updates	New features
Important security updates	Quality fixes
Limited update-related technical support	Design changes
	General technical support

Pricing follows a cumulative model where costs double annually. Organizations enrolling in Year 2 must pay both Year 1 and Year 2 fees. Three-year maximum coverage applies to all products.

Product-Specific Migration Paths

Windows Server 2016

• Primary migration target: Windows Server 2025
• ESU availability: Up to 3 years post-January 2027
• Pricing: To be announced in coming months

Windows 10 Enterprise LTSB 2016

• Recommended targets:
  • Windows 11 Enterprise LTSC 2024 (for compatible hardware)
  • Windows 10 Enterprise LTSC 2021
• ESU pricing:
  • Year 1: $61/device ($45 with Intune/Autopatch management)
  • Year 2: $122/device ($90 managed)
  • Year 3: $244/device ($180 managed)
• Availability: Q2 2026 via Volume Licensing or CSP

Windows IoT Enterprise LTSB 2016

• Upgrade paths:
  • Windows 11 IoT Enterprise LTSC 2024
  • Windows 10 IoT Enterprise LTSC 2021
• ESU procurement: Exclusively through OEM partners
• Pricing: Manufacturer-specific (cumulative structure applies)

Strategic Recommendations

1. Prioritize hardware assessment: Windows 11 LTSC requires modern hardware specs. Begin compatibility testing immediately.
2. Evaluate ESU economics: Calculate cumulative costs against migration expenses. Managed devices see 26% Year 1 discounts.
3. IoT specialization: OEM-dependent ESU procurement requires early manufacturer engagement.
4. Leverage management tools: Intune/Autopatch users gain pricing advantages and streamlined update deployment.

While ESU provides breathing room, Microsoft emphasizes migration to supported LTSC versions as the optimal path. Enterprises should reference the Extended Security Updates FAQ and Microsoft Lifecycle documentation for detailed planning. Complex environments should initiate migration projects now to avoid compounded ESU expenses and security risks.