Microsoft will end extended support for Windows 7 and Windows Server 2008 R2 on January 14, 2020. After this date, these operating systems will no longer receive free security updates or technical support. This discontinuation poses risks for organizations with regulatory obligations, as they may struggle to maintain compliance. While systems will continue to function, using unsupported software increases vulnerability to malware and security threats. Unpatched vulnerabilities could lead to the loss of data confidentiality, integrity, and availability. Mission and business operations reliant on these systems could suffer significant negative consequences. The Cybersecurity and Infrastructure Security Agency (CISA) advises upgrading to a newer operating system. Organizations should identify affected devices and develop a plan for migration. Exploring fee-for-service maintenance options with the vendor is also recommended if immediate upgrades are not feasible. Federally certified voting systems running Windows 7 will receive free updates through the 2020 election.