Described herein are systems and methods for aggregating, parsing, and annotating regulatory context for use in resolving transactional inquiries. In one embodiment, a method comprises: aggregating documents from a plurality of data sources and storing the aggregated documents in a document database; selecting a first document from the document database; extracting regulatory content from the first document; parsing the regulatory content into a structured data object; identifying a substantively-relevant portion of the regulatory content in the structured data object; generating an annotation associated with the substantively-relevant portion; storing the generated annotation in an annotation database; and generating a domain-specific data structure for resolving transactional inquiries based on the annotation database.