Microsoft Sells Time for Legacy Exchange and Skype
Microsoft is turning end-of-life messaging into a paid stopgap. If Exchange Server 2016/2019 or Skype for Business Server 2015/2019 are still in service, the real choice is now between paying for temporary coverage or finishing a migration under a hard deadline; patching later is not a plan because the support window itself is closing.
Microsoft will offer a second Extended Security Updates period for Exchange Server from May 2026 to October 2026, after the first six-month ESU window ends in April 2026. The same approach applies to Skype for Business Server 2015 and 2019, with customers required to pay and no guarantee that updates will actually be released during the extension.
The forward risk is not just cost. The short window pushes late migrations into a compressed schedule, which raises the chance of rushed cutovers and leaves any remaining legacy deployments dependent on a program Microsoft says will not be extended again.