A machine learning computing system identifies a vulnerability associated with a server. Based on information associated with the server and a knowledge base, the computing system schedules an interval for patching the server in a centralized tracking module. Based on the knowledge base and the vulnerability, the computing system creates, validates, and deploys the patch job. During patch job execution, the computing system monitors the status of the patch job at the server and transmits status updates to a user interface module. After expiration of the interval, the computing system generates an assessment report for the executed patch job. The computing system updates the knowledge base based on the assessment report to improve future decisioning processes. Based on the success or failure of the patch job, the computing system, upon a failure indication, automatically reschedules an interval for patching the server.