Marked by difficulty falling or staying asleep and/or poor sleep leading to daytime dysfunction, insomnia contributes to functional impairment, poor health, and increased healthcare utilization when left untreated. As many as two-thirds of Iraq and Afghanistan military veterans complain of insomnia. Older veterans of prior conflicts report insomnia occurring since initial service, suggesting a chronic nature to insomnia in this population. Despite insomnia's high prevalence and severe consequences, there is no theoretical model to explain either the onset or chronicity of insomnia in this growing patient population. Existing theories view insomnia as an acute, unidirectional phenomenon and do little to elucidate long-term consequences of such problems. Existing theories also fail to address mechanisms by which acute insomnia becomes chronic. This paper presents an original, integrated theoretical model that draws upon constructs from several prominent behavioral medicine theories to reconceptualize insomnia as a chronic, cyclical problem that is both a consequence and predictor of stress. Additional research examining the relationships between stress, sleep, resilience, and outcomes of interest could inform clinical and research practices. Addressing sleep problems early could potentially enhance adaptive capacity, thereby reducing the risk for subsequent negative outcomes.