Insomnia remains a common complaint for which patients present to their primary care providers. The reflex response by most primary care providers to treat insomnia is by prescribing hypnotics. The most commonly prescribed hypnotic is a sedative, such as a benzodiazepine or a benzodiazepine receptor agonist (BRZA). Paradoxical insomnia is a subtype of insomnia described as a complaint of severe insomnia disproportional to the presence of objective sleep disturbance or daytime impairment. Previously known as sleep-state misperception, this subtype of insomnia is not well known among the primary care community. We present a case of a 60-year-old female who had been prescribed multiple hypnotics for over 10 years and presented to our sleep clinic frustrated due to failure of treatment with each medicine. She was eventually diagnosed with paradoxical insomnia after an evaluation of her sleep parameters. This was effectively treated with cognitive-behavioral therapy. This case report aims to raise awareness of this subtype of insomnia in patients at the primary care level and to help minimize the use of hypnotics.