Insomnia is widely recognized as a prevalent and complex condition with significant variation in prevalence depending on the definitions and diagnostic criteria applied, ranging from 5% to 50% in global literature. One-third of adults report insomnia symptoms, although rates decrease when daytime functional impairment is considered. Eagle syndrome (ES), particularly the jugular variant (JES), has been associated with insomnia, chronic pain, and tinnitus, suggesting an intertwined relationship between sleep disturbances and pain pathways. Chronic pain conditions, including ES, often demonstrate central sensitization, where poor sleep exacerbates pain sensitivity and vice versa. Neurotransmitter pathways, particularly dopaminergic and serotonergic, are implicated in both pain modulation and sleep regulation, thus providing a potential shared pathophysiological basis for insomnia in chronic pain patients. A descriptive study on 19 Italian patients with classic ES found a significant prevalence of insomnia (73.7%), persisting post-surgery despite resolution of painful symptoms. This highlights the role of perpetuating factors in insomnia, supporting the hypothesis that sleep disturbances can develop as independent clinical entities. Current guidelines recommend Cognitive-Behavioral Therapy for Insomnia (CBT-I) as the preferred treatment for insomnia comorbid with chronic pain, targeting behavioral and cognitive perpetuating factors. This study suggests the necessity of insomnia-specific treatment alongside surgical intervention for ES. Future research is encouraged to examine insomnia across different ES variants to better understand and treat this comorbidity.