The present disclosure is directed toward systems and methods for dynamically providing digital content to client devices at different insertion points of a digital video based on predicted total value of inserting the digital content and predicted engagement loss of inserting the digital content. For example, system and methods described herein determine that an insertion point is approaching in an actively playing digital video. In response, systems and methods identify digital content for insertion at the insertion point. In one or more embodiments, the described systems and methods insert the identified digital content by comparing the predicted total value of inserting the digital content at the insertion point of the digital video and a predicted engagement loss associated with inserting the digital content at the insertion point of the digital video.