A system is provided for resolution of technical issues using computing system-specific contextual data. In particular, the system may comprise a software-based automated security agent that may run in the memory of a computing system within a network. The security agent may continuously monitor the computing system to capture precise information about the computing system at all points in time. When the computing system encounters a technical issue, the system may then use the data collected by the security agent to execute a search within a resolution database to provide a solution to the technical issue. In some embodiments, the system may further comprise a remediation engine which may cause the security agent to automatically implement the solution. In this way, the system provides an expedient way to resolve technical issues in computing systems within the network environment.