Microsoft is set to retire a cluster of widely used products and services in October 2026, creating a compressed deadline for IT administrators to plan upgrades or migrations. The timing means several major end-of-support dates land within weeks of each other, raising the risk of disruption for organisations that fail to prepare, particularly those relying on on-premises Microsoft software rather than cloud-based Microsoft 365.

Among the casualties are Office LTSC 2021 (covering Access, Word and the rest of the suite), which requires a move to LTSC 2024 or Microsoft 365 to retain support, and Windows Server 2022, which exits mainstream support on 13 October 2026 (extended support runs to 2031). Windows 11 24H2 Home and Pro end on the same date, while 23H2 for enterprise and education gets until 10 November. Microsoft Publisher 2021 will also be discontinued in October, ending a 35-year product line with no direct replacement, and Entra ID Sign-In risk policies are retired on 1 October 2026, with Microsoft urging admins to migrate to Conditional Access beforehand. By contrast, October 2027 is expected to be quieter, with only SQL Server 2017 due to lose support.