Microsoft has acknowledged that the Windows Server security updates released on October 13, 2026, may disrupt Exchange Server email services, affecting on-premises systems running Exchange Server 2016, 2019, and the Subscription Edition. The disruptions can include blocked webmail access and undelivered messages. Microsoft has identified four specific Windows updates linked to these issues: KB5126646 for Windows Server 2025, KB5126655 for Windows Server 2022, KB5126651 for Windows Server 2019, and KB5126868 for Windows Server 2016. Symptoms may include inability to log into Outlook on the web, messages stuck in the Outbox, increased mail queues, and failed mailbox access. A critical error to monitor is MapiExceptionMdbOffline, and affected systems may log Event ID 1006. The October updates introduced a default limit of 512 simultaneous Endpoint Lookup calls, which can be exceeded under heavy Exchange workloads. Microsoft has provided a registry workaround to increase this limit and suggests monitoring for recurring failures. The disruption coincides with the end of the final paid update period for Exchange 2016 and 2019, with future updates limited to the Subscription Edition.