Indeed, the incorporation of AI-enhanced feedback systems into the educational environment is an important innovation that helps to initiate more student responsibility and sensitivity. Thus, such systems offer increased potential for better learning outcomes through metacognition, self-regulation, and intrinsic motivation of students. This chapter discusses how AI shapes behaviors in the learner population in digital learning environments and massive open online courses (MOOCs) which are highly sensitive to instructors considering problems of engagement and discipline with large cohorts. The current study uses a qualitative research design that works through a descriptive literature review to an analytical assessment of AI systems’ implications and effectiveness. From the scholarly point of view, what comes out of the research is that AI-enhanced feedback systems do not only solve problems related to plagiarism and academic dishonesty but also build trust and effort within the learner population. It is the implementation of AI feedback systems that can, through the channels of regulation transformation, make students’ accountabilities more self-regulated and education motivations more self-realized. Such findings could inspire several other ideas and creations about what artificial intelligence could do for and with education.