This chapter presents Highly Interactive Digital Narrative (HIDN) as a vision for future Interactive Digital Narratives (IDNs) offering a higher degree of interaction possibilities and more reactive/generative narrative potential than currently possible. It discusses some issues of relevance to the application of artificial intelligence (AI) to interactive narrative, with the objective of pointing at possible future developments of the IDN field. In some AI applications, the intelligent system is in direct interaction with a user: automatic recommendation systems, intelligent tutoring systems, interface agents, search engines and interactive storytelling. Finally, the chapter concludes the core challenge of highly interactive digital narrative, which is merging narrative coherence and user intervention, has been analysed from various perspectives leading to the simple conclusion that the problem is fundamentally ill-defined; therefore, its current solutions need to be rethought. Moving from a problem solving to a creative perspective, people redefined the priorities for future research in the domain.