Fuente: Wipo "digitalization" The present disclosure is directed toward systems, methods, and non-transitory computer readable media that provide a contextual content generation system that trains and implements a unique machine learning architecture to generate context-specific digital content items based on a digital guideline document. In particular, the disclosed systems select a content generation method from among prompt engineering and/or updating one or more machine learning models to generate digital content. For example, the disclosed systems utilize machine learning models to extract key elements from a digital guideline document comprising context-specific guidelines for digital content. Further, the disclosed systems generate an augmented prompt comprising indications of key elements from the digital guideline document. In addition, the disclosed systems select a content generation method from among prompt engineering and/or updating machine learning models to generate the digital content item which incorporates digital content corresponding to the context-specific guidelines based on the augmented prompt.