A study examined parent-reported perceptions of wheelchair headrests for children with severe physical disabilities. It involved 79 participants, including children aged 2 to 25, who assessed the usability and impact of headrests after a two-week trial. Most participants were male (64%) and had cerebral palsy (55%). Three headrest types were primarily used: Headaloft (30%), posterior support headrests (24%), and the 360 system by Headovations (16.5%). Overall usability was rated high, averaging 82.4 out of 100. Parents reported notable improvements in their children’s communication (73%), eye contact (68%), and positioning during transportation (68%). Additionally, there were enhancements in feeding, breathing, and reduced fatigue. No significant differences were found between the various headrest types. The study emphasizes the value of parent feedback in evaluating head support systems for children with disabilities, particularly when headrests are customized by experienced therapists.