Many chronic insomnia patients use sleep medication well beyond the recommended duration, and patients who are hypnotic-dependent encounter several challenges when attempting to discontinue. The current article presents these challenges and reviews studies that have added cognitive-behavioral therapy for insomnia (CBTI) to a gradual tapering program to facilitate discontinuation of hypnotic medication in chronic insomnia patients. The current literature provides substantial support for using CBTI to facilitate discontinuation of hypnotic medication in chronic insomnia patients. Across several randomized clinical trials, the majority of the findings indicate that using CBTI, delivered by a therapist or self-help, along with a supervised or gradual tapering program is superior to tapering only or CBTI only in terms of medication discontinuation. Although these results are promising, it should be noted that the long-term evidence is more equivocal, as over 40% of patients relapse in the need for sleep medication within 2 years, which may highlight the importance of adding follow-up booster sessions in hypnotic-dependent insomniacs. These findings indicate that rather than choosing between CBT and hypnotic medication, clinicians might be better served using both treatment modalities to optimize the relative strengths of each treatment. Such an approach represents a more modern view of treating chronic insomnia patients by using both pharmacological and non-pharmacological tools.