An expert diagnostic agent for use in diagnosing intermittent and/or difficult to reproduce software failures in computing devices is disclosed. The expert diagnostic agent gathers data about the operating system of a computing device and a plurality of software components coupled to the computer operating system; applies rules to the data to identify software failures; invokes tools as needed to attempt to correct the software failures; and reports information about software failures. The expert diagnostic agent may be invoked directly or activated by certain events in computer system.