The primary goal of amplification is to restore audibility without causing discomfort; for someone with severe-to-profound hearing loss, the reduced dynamic range poses unique challenges in hearing-assistive device fitting. These challenges, including physiological limitation, processing difficulties, technology constraints, and other confounding factors, must be considered when selecting, fitting, and counseling for appropriate amplification. Many of the advanced features in hearing aids do not adequately address the unique characteristics of patients with severe-to-profound hearing loss. This review article will attempt to unravel some of the challenges and associated considerations when fitting adults and children with severe-to-profound hearing loss.