Military noise environments, and, in particular, the noise environments faced by dismounted soldiers on the battlefield, are characterized by wide variations in ambient level. Situations can quickly and unexpectedly change from quiet conditions where the sound of a snapping twig might alert the listener to hostile enemy activity to extreme noise conditions where firefights, explosions, or loud machinery create levels of noise that can cause hearing loss in a matter of minutes or seconds. This poses a unique challenge for the designers of military hearing protection, who must produce systems that provide enough comfort and acoustic transparency to convince users to consistently wear them in quiet conditions to ensure that they will be in place if an unexpected blast or other potentially damaging noise exposure occurs. In this talk, we discuss some of the issues that can influence the willingness of listeners to wear hearing protection for extended periods in quiet environments, including acoustic factors that have been shown to influence situational awareness while wearing hearing protection. Additionally, lessons on the factors impacting the comfort of hearing devices drawn from studies of how consistently hearing aids are worn by hearing impaired listeners will be discussed.