An earbud tip for an in-ear headphone can include an outer body; an inner tube extending at least partially within the outer body, the tube having opposing first and second ends and first and second openings at the opposing first and second ends, respectively, the first opening configured to emit audio signals provided by a speaker of an in-ear headphone into a user's ear canal during operation of the in-ear headphone and when the earbud tip seals the user's ear canal and the second opening configured to be removably coupled to a portion of the in-ear headphone; and one or more channels extending from an outer periphery of the earbud tip to the inner tube.