Sleeplessness - a universal experience with a variety of causes - may be increasingly diagnosed and treated as the medical condition insomnia, or medicalized. This research provides quantitative and qualitative evidence of the medicalization of insomnia at the level of patient-physician interaction. I analyze 14 years (1993-2006) of data from the National Ambulatory Medical Care Survey, a nationally representative dataset of physician office visits. I describe trends over time for: complaint of sleeplessness, diagnosis of insomnia and prescription of sedative hypnotics (select benzodiazepines, Trazodone and non-benzodiazepine sedative hypnotics [NBSHs]). Independent variables are age, gender, race and insurance status. To measure change over time, I conduct linear regressions using weighted visits, calculate slope estimates and report P-values. I also carry out semi-structured qualitative interviews with patients (N=27) prescribed a sedative hypnotic, and their physicians (N=8). Between 1993 and 2006 complaint of sleeplessness increased 30% (3.3 million to 4.7 million); diagnosis increased 6-fold (869,000 to 5.2 million) and prescriptions for all sedative hypnotics increased. Most notable was the 23-fold increase in NBSHs (550,000 to 12.8 million). Slope change and differences in proportion were positive and significant for insomnia diagnoses, NBSHs and Trazodone. Female gender was significantly associated with prescriptions of Trazodone. Patients 55+ were significantly more likely to receive a prescription for a benzodiazepine or a NBSH. Physicians were cognizant and critical of medicalization. They conceptualized insomnia as a symptom, part of the aging process, or a reaction to stress - not a disease. Despite stated bias, respondents prescribed sleep aids at least some of the time. Compliance was influenced by time constraints, consumerism, and pre-existing prescriptions. Patients entered their office with medical knowledge from non-medical sources including the Internet, social networks and direct to consumer advertising. Patients said that insomnia was a symptom of stress, anxiety or comorbid illness. Fear of addiction to sleep aids was common. Factors mediating their physician interaction were time constraints, pre-existing prescriptions and consumerism. These data elucidate both the increased medicalization of sleeplessness and micro and macro fueling factors. Even when not formally re-defined as insomnia, sleeplessness is increasingly treated with medical solutions.