Windows Server 2016 End of Support (Jan 12, 2027): Upgrade, ESU or Move? What Each Path Costs

Windows Server 2016 stops getting free security fixes on January 12, 2027. Three years of extended updates cost $2,999 per 16-core Standard host, a… Aliteq 0xLax · Founder · Cloud & Infrastructure

Windows Server 2016 reaches end of support on January 12, 2027. After that, Microsoft sells Extended Security Updates (ESU) for up to three years. Through Azure Arc they cost $83.30 a month for a…

Deadline: January 12, 2027; paid updates bill from January 13

ESU via Azure Arc: $2,999 per 16-core Standard host over 3 years

Windows Server 2025 Standard: $1,176 per 16 cores, plus CALs

Upgrade path: 2016 goes straight to 2025 with installation media

Azure: ESU free for 3 years, compute billed

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