Administrators still using Windows Server 2016 face a January 12, 2027 deadline for the end of extended support. Microsoft says January’s security update will be the release’s last, ending monthly security fixes for the decade-old operating system, BleepingComputer reported on October 23.
Every Windows Server 2016 edition is covered: Datacenter, Essentials, MultiPoint Premium and Standard. The cutoff also ends support for the Essentials features, including Remote Web Access and other Essentials-specific functionality. Systems that remain on the release after its final update will no longer receive monthly protections against newly addressed security threats.
The deadline completes a support lifecycle that began with general availability on October 12, 2016, following the release’s introduction at Microsoft’s Ignite conference that September. Mainstream support ended in January 2022; extended support has continued since then.
Microsoft recommends that administrators prepare to move to Windows Server 2025 before the cutoff. That release entered Windows Insider distribution in January 2024 and became generally available in November 2024. It is the latest Windows Server Long-Term Servicing Channel (LTSC) release.
According to Microsoft’s lifecycle information cited by BleepingComputer, Windows Server 2025 has mainstream support until November 2029, with another five years of extended support ending on November 14, 2034. Microsoft also offers a free 180-day trial through its Evaluation Center for organizations evaluating the release before deployment.
Authentication compatibility is one consideration for that evaluation. Microsoft’s Credential Guard guidance says upgrades to Windows Server 2025 enable the feature by default unless it is explicitly disabled. The company advises organizations to test their operational scenarios before updating devices that use Credential Guard.
With the feature enabled, CredSSP loses access to saved credentials and single-sign-on credentials, although users can still supply cleartext credentials. The Remote Desktop client also cannot send saved Windows credentials to a remote host; attempts fail with the message Logon attempt failed. These documented restrictions can affect authentication workflows during a move to the newer server release.
