Listening comprehension has had a long and ever-evolving history. Within the last 100 years, we have seen it progress from analog phonograph recordings, through the audiotape era, and into the digital realm. Questions arise as to how this evolution has proceeded, what pitfalls and accomplishments we have experienced, and where we might envision aural comprehension technology and its support of second language acquisition in the future. This article addresses the history of listening comprehension technology, presents numerous questions and answers (as they stand today) with regard to the benefits of modern listening comprehension technology, and offers suggestions as to how we can better ensure success with digital technologies and aural comprehension in the future. (Contains 2 figures.)