A self-fitting device for location in an ear canal. The device includes a body having a body ear end, an opposite body user end, and a shaft extending from the ear end to the user end. A resilient bladder is joined with the body ear end and a chamber is defined inside the resilient bladder. An elongate plunger is located in the shaft. The resilient bladder is deformable between an at-rest position and an in-ear position. The elongate plunger actuates between the at-rest position and an insertion position to assist the resilient bladder to be deformed into the in-ear position. The plunger actuates in the insertion position without extending a front end portion of the bladder forward of a position of the front end portion when the bladder is in the at-rest position.