Recent evidence suggests that sleep disturbance may play an important role in the development of cardiovascular disease (CVD). Despite the prevalence of sleep complaints among service members of recent military conflicts, few studies have examined associations between sleep and risk factors for CVD in this population. Symptom checklist items regarding distress about “trouble falling asleep” and “restless/disturbed sleep” were used as proxies for sleep onset and maintenance difficulties to examine these associations in US military service members of recent conflicts. Veterans having both sleep onset and maintenance difficulties had greater odds of being a current smoker and having psychiatric symptoms and diagnoses. Increased odds of a self-reported hypertension diagnosis and elevated systolic blood pressure were also found in certain subsets of this sample. Findings highlight the need for greater recognition of sleep difficulties as a CVD risk factor in a population known to be at increased risk for this condition.