This qualitative research study was designed to inform the development and implementation of effective online learning environments by exploring, from both teacher and student perspectives, what constitute effective online learning experiences. The study examined course content, tasks, and pedagogical approaches, as identified by students and instructors, which contributed to or hindered positive online learning experiences. Researchers interviewed 6 online course instructors and 10 adult students to understand their experiences in undergraduate and graduate level online degree programs. Using a Cognitive Apprenticeship Model to inform the analysis of data, findings revealed an emphasis on text-based content and lecture; instruction that led to disconnect between students, teachers, and course content and goals; and one innovative program that links real-world experiences with online classroom learning. Given the growing number of online programs, the study provides insight for course development and pedagogy as well as offers possibilities for additional research.