A contextual analysis engine systematically extracts, analyzes and organizes digital content stored in an electronic file such as a webpage. Content can be extracted using a text extraction module which is capable of separating the content which is to be analyzed from less meaningful content such as format specifications and programming scripts. The resulting unstructured corpus of plain text can then be passed to a text analytics module capable of generating a structured categorization of topics included within the content. This structured categorization can be organized based on a content topic ontology which may have been previously defined or which may be developed in real-time. The systems disclosed herein optionally include an input/output interface capable of managing workflows of the text extraction module and the text analytics module, administering a cache of previously generated results, and interfacing with other applications that leverage the disclosed contextual analysis services.