A method of encoding knowledge is disclosed, which can be used to automatically detect problems in software application deployments. The method includes accessing a source of knowledge describing a problem known to occur in deployments of a particular software application, and which identifies a plurality of conditions associated with the problem. An encoded representation of the knowledge source is generated according to a predefined knowledge encoding methodology. The encoded representation is adapted to be applied automatically by a computer to analyze data representing a current state of a monitored deployment of the software application to detect whether the conditions and the problem exist therein. In various implementations, the encoded representation of the knowledge can include queries for deployment information, information concerning the relative importance of the conditions to a detection of the problem, and/or logical constructs for computing a confidence value in the existence of the problem and for determining whether to report the problem if some of the conditions are not true. The knowledge source can comprise a text document (such as a knowledge base article), a flowchart of a diagnostic troubleshooting method, and the like. Also disclosed are methods of at least partially automating the encoding process.