Disclosed embodiments provide techniques to identify the in-context meanings of natural language in order to decipher the evolution or creation of new vocabulary words and create a more holistic user experience. Thus, disclosed embodiments improve the technical field of digital content comprehension. In embodiments, machine learning is used to identify sentiment of text, perform entity detection to determine topics of text, and/or perform image analysis on images used in digital content. Words, symbols, and images that are determined to be potentially unfamiliar to a user are augmented with a supplemental definition indication. Invoking the supplemental definition indication enables rendering of additional definition information for the user. This serves to accelerate understanding of digital content such as webpages and social media posts.