Embodiments are generally directed to techniques for extracting contextually structured data from document images, such as by automatically identifying document layout, document data, and/or document metadata in a document image, for instance. Many embodiments are particularly directed to generating and utilizing a document template database for automatically extracting document image contents into a contextually structured format. For example, the document template database may include a plurality of templates for identifying/explaining key data elements in various document image formats that can be used to extract contextually structured data from incoming document images with a matching document image format. Several embodiments are particularly directed to automatically identifying and associating document metadata with corresponding document data in a document image, such as for generating a machine-facilitated annotation of the document image. In some embodiments, the machine-facilitated annotation of a document may be used to generate a template for the template database.