Eol on CuraSec

Windows Server 2016 reaches end of support January 2027

Sat, 24 Oct 2026 14:29:02 +0000

Engineer — Plan: With roughly three months until the January 2027 deadline, audit your estate now for Windows Server 2016 instances and schedule migration to Server 2022/2025 or enroll in Extended Security Updates before the cutoff.
SOC/IR — Skip
Leader — Plan: Inventory Windows Server 2016 dependencies across the org this quarter, budget for migration or ESU licensing, and flag to IT ownership — unpatched post-EOL servers will widen audit exposure and increase breach risk from future unpatched CVEs.

Thu, 15 Oct 2026 15:35:13 +0000

Engineer — Plan: Server 2022 now receives security patches only (no new features) through October 2031; audit your Server 2022 fleet and add a migration milestone to a supported release before extended support ends.
SOC/IR — Skip
Leader — Plan: EOL transition for a widely deployed server OS is a budget and roadmap input — schedule a migration plan from Server 2022 well before the 2031 extended support cutoff to avoid compliance gaps and unsupported infrastructure risk.

Fri, 09 Oct 2026 17:26:04 +0000

Engineer — Plan: Audit the estate for devices running unsupported Windows versions and schedule upgrades before the Windows Update certificate rotation deadline next year — after that point, those devices will be permanently cut off from security updates.
SOC/IR — Skip
Leader — Plan: Request an inventory of unsupported Windows endpoints from the engineering team; devices that fall off the update chain raise compliance risk under frameworks like PCI DSS and SOC 2, and increase exposure to unpatched vulnerabilities — factor upgrade budget into next quarter’s planning.