Microsoft has announced the impending end of support for Windows Server 2016 on January 12, 2027, along with Windows 10 Enterprise LTSB 2016 and Windows 10 IoT Enterprise LTSB 2016 on October 13, 2026, after which these versions will no longer receive security patches, bug fixes, or technical assistance. Organizations still relying on these legacy systems risk increased vulnerability to cyber threats once final updates are delivered. Microsoft urges customers to upgrade to modern alternatives like Windows Server 2025 or newer Windows 10/11 LTSC releases for continued security and compliance. Extended Security Updates (ESU) will be available for up to three years post-support as a paid, security-only bridge option.