The author argues that the online environment lends opportunities for development of critical thinking and creation of a collaborative learning environment not available in the face-to-face classroom. The author compares student participation, test results, the quality of writing assignments in art history survey courses she taught online and face to face at the same university. Not only can critical thinking be encouraged and facilitated by introducing challenging and intriguing topics in group discussions and blogs, but the specific nature of online communication provides a unique and positive atmosphere for discussion: anonymity fosters participation among students who are less fond of public speaking, schedule flexibility means students can do research before posting to discussion boards, a lack of time constraints means discussions do not have to “end” when “class” is over, visibility of discussion postings to the entire class means that students can and do learn from their peers, and the variety of available tools means students can incorporate images, audio/video clips and graphics into their analytical reflections. This paper summarizes the most effective approaches taken to establishing group discussions in asynchronous online courses, discusses learner engagement strategies in the e-learning environment, describes best practices for the optimal use of discussion boards, analyzes learning outcomes of discussion board assignments compared to in-class essays and writing assignments.