A system for troubleshooting a network, the system comprising a virtual machine including a virtual central processor in communication with at least one memory, virtual machine including a knowledge base configured to store contextual information related to the network; a knowledge base manager in communication with the knowledge base, the knowledge base manager configured to collect at least one of contextual information and problem information from at least one data source on the network and populate the knowledge base; a problem monitor in communication with the knowledge base and the knowledge base manager, the problem monitor configured to receive the problem information from the knowledge base manager; a query evaluation engine in communication with the knowledge base and the problem monitor; an interface configured to receive a query; and a natural language query translator in communication with the interface and the query evaluation engine; wherein the natural language query translator is configured to provide a natural language query from the interface and transmit the query in a machine readable format to the query evaluation engine; wherein the query evaluation engine collects at least one of the contextual information in the knowledge base and the problem information in the problem manager relevant to the query and generate a recommendation list.