2026 has begun with the familiar sound of Microsoft’s software Grim Reaper sharpening a blade as administrators peer glumly at the calendar of carnage ahead.

Some big beasts face the chop this year. Office LTSC 2021 reaches end of the road on October 13, alongside the final Extended Security Updates for Windows Server 2012 and 2012 R2. SQL Server 2016 also transitions to Extended Security Updates.

Then there’s a raft of Azure retirements. March sees the demise of Speech to Text API v3.0, followed by Windows Server 2016 on AKS hybrid and Windows Server 2019 on AKS. Application Gateway v1 – which stopped accepting new deployments in 2024 – will be forcibly stopped on April 28, 2026.

Windows 11 Home and Pro 24H2 hit end of support on October 13, as does the veteran Microsoft Publisher, with no real replacement in sight for customers who need to dash off the odd certificate or two.

Legacy authentication services retirement might trip up administrators. From January 31, legacy client authentication will be blocked by default for SharePoint Online and OneDrive for Business. The block can be lifted for a few months, but becomes permanent from May 1. The Identity Client Run Time Library (IDCRL) is on its way out.

SharePoint versions 2016 and 2019 reach the end of support on July 14, along with Project Server 2016 and 2019. SharePoint Server 2016’s demise finally allows Microsoft to kill off InfoPath 2013, kept alive solely for compatibility.

The list goes on, and serves to highlight that while 2025 marked the end for most Windows 10 versions, 2026’s retirement roster is equally demanding of administrator attention and planning.

Microsoft has given ample notice, but many enterprises tend to operate on a basis of “if it ain’t broke, don’t fix it”, particularly if a fix requires handing cash to Microsoft and its partners. Administrators would be wise to take a long look at 2026’s farewells and plan accordingly.