Abstract: A system and method for generating secondary advertising content for presentation on a user interface of a device in association with primary publishing content. The system and method comprise a queue for receiving the primary content including a plurality of identifiable textual elements for analysis as candidates to associate with the secondary content. The plurality of identifiable textual elements are distributed in a number of defined regions of the primary content such as paragraphs. The system and method also have a content analyzer module configured for accessing the primary content and for performing a contextual analysis of the plurality of identifiable textual elements. The analysis includes determining for each of the number of defined regions those key elements from the identifiable textual elements that match element entries in at least one key element list. The analysis further includes determining a density of the matched key elements from a specified region of the number of defined regions.