The recent breathtaking progress made in generative natural language processing (NLP) has been propelled by large language models and innovative learning methods that intersects machine learning (ML) and NLP such as Reinforcement Learning with Human Feedback (RLHF), leading to the creation of impressive chatbots like ChatGPT. However their lack of groundedness, factuality, and interoperability with tools and custom APIs limits them to mostly creative endeavors due to low fidelity and reliability. On the contrary, digital assistants in the real world such as Siri, Alexa, and Google Assistant can interface with proprietary APIs, but they still cover a relatively narrow set of use cases that are mostly simple single-turn interactions. Through the combination of each of their strengths, the goal of deploying truly conversational and capable digital assistants that are also trustworthy seems tantalizingly close. What are the remaining challenges for this goal, and how can the ML and NLP communities come together to overcome them? The goal of this workshop is to bring together machine learning researchers and dialogue researchers from academia and industry to encourage knowledge transfer and collaboration on these central questions to discover ideas that can further expand the use cases of conversational AI. The ideal outcome of the workshop is to identify a set of concrete research directions to enable the next generation of digital assistants.