Before applying any updates to your Windows Server, it is essential to have a well-thought-out plan that covers what, when, and how you will update. Different factors must be taken into account, such as the type and frequency of updates (monthly cumulative updates, security-only updates, or optional updates), the update source (Windows Update, Windows Server Update Services (WSUS), or a third-party tool), and the update schedule (off-peak hours or maintenance windows). Additionally, you should notify users and stakeholders about the expected downtime and impact and test your updates in a non-production environment before deploying them to your live servers. Finally, having a backup and restore plan is necessary in case something goes wrong.