Karpinski 2000 describes “Gestalt hearing,” identifying chords instantly and holistically, as the ideal endpoint of training in harmonic dictation. Yet the subdominant chord (e.g.) is not a single object but a collection of objects that differ in timbre, texture, inversion, spacing, etc. Is it really possible to become so acquainted with this group that one perceives it as a Gestalt? If so, what experiences and abilities are necessary to develop Gestalt hearing? This article draws on relevant results from an observational, exploratory study of harmonic listening (N=73) to suggest preliminary answers to these questions and paths for future research in this area. Our results suggest that Gestalt hearing, if it exists, may not be available in college-level instruction.