It is common knowledge by now that Microsoft will end-of-life Windows Server 2003 as of July 14, 2015 and no longer provide software maintenance or support. In other words, Microsoft will stop issuing software updates for patching software vulnerabilities discovered. Unfortunately, this is a cause of great concern for many organizations that are still running Win2K3 servers and may take some time before they can migrate these workloads to alternative operating systems. Organizations planning on continued use of Windows Server 2003 must implement compensating controls to add defense-in-depth protection and enhanced security monitoring capabilities. Trend Micro’s Deep Security product can be helpful here by providing network, system and anti-malware security controls across physical, virtual, and cloud systems running W2K3.