A contextual index compendium that includes contextual index item generation rules that define document index entry generation transforms usable to transform text of the documents into embedded document index entries of document indexes within the documents is obtained by a processor. Using the document index entry generation transforms defined within the contextual index item generation rules in association with a document that includes embedded document index entries that are both embedded at locations of associated text distributed throughout the document and added as part of a document index within the document, new text of the document is programmatically transformed into at least one new document index entry in response to determining that at least one portion of the new text includes candidate text that is not already indexed within the existing embedded document index entries and the document index within the document.