Advancements in Artificial Intelligence (AI) have potentially created new ways to teach and learn, such as the use of Learning Analytics (LA) to monitor and support students using data captured in Learning Management Systems (LMS). To add human rather than data-based support, in this chapter, we present our use of AI-enabled Pedagogical Conversational Agents (CAs) over the past 12 months in multiple units/subjects across two universities. These CAs play a role similar to a teacher or peer learner by sharing the expertise they have acquired from the knowledge contained in student–teacher social interactions in LMS forums and grade book teacher feedback. Unlike teachers or peers, these CAs can be contacted anonymously at any time, they don’t mind being asked the same question repeatedly and they can empower students to explore options and outcomes. We conclude the chapter with a discussion of the potential of LA to automate CA interactions.