A deep insert, inflatable hearing protection earplug is provided that is easy for an untrained user to insert correctly, reliably providing high acoustic attenuation and remaining both secure and comfortable for long durations in a human ear. The earplug comprises a soft elastomer shell that forms a sealed volume filled with an inert fluid. The earplug can comprise a slender, flexible stem that is easily insertable into the ear canal when deflated. The proximal end of the earplug can be situated outside the ear canal, within the concha of the ear, and incorporates a bulb with a hemispherical, bistable cap. After inserting the shaft of the earplug into the ear canal, the wearer applies force with a finger to invert the cap, which transitions elastically from a convex to a concave external geometry, displacing a fixed volume of fluid to inflate a sheath that forms the outer covering of the stem, filling and sealing the ear canal. The sheath can be deflated by pulling on or otherwise engaging a release tab or other feature attached to the cap.