Melatonin is an easily accessible, widely used drug for sleep issues, disrupted sleep–wake cycles, and jet lag, available in a variety of forms and dosages. Melatonin is also used in hospital settings to promote sleep onset, particularly in elderly patients, as a circadian rhythm regulator. Despite the popularity of melatonin, it is not approved by the US Food and Drug Administration (FDA). This creates ambiguity surrounding its proper usage for optimum results, including dosage and time of administration. The objective of this article is to shed light on the best timing to administer melatonin. Melatonin is a hormone that our body naturally produces to regulate our biological clock. Even though our body has a built-in “sleep system,” many people still suffer from chronic sleep disorders such as insomnia. Melatonin has also proved to help prevent delirium in hospitalized patients due to its circadian rhythm regulatory effects. The elderly are at risk of developing insomnia because as one ages, melatonin production decreases. The most convenient solution for insomnia is to take melatonin supplements. To optimize the effects of melatonin supplements, proper dosage and timing must be considered. Additionally, patients who are oppositional to bedtime, which is known as bedtime resistance, are typically more willing to go to bed following melatonin administration. Melatonin administration at around 6 PM (1–2 hours before bedtime) is optimal to regulate sleep cycles of patients, and it can help with bedtime resistance. This should be the standard of care in all hospitals, nursing homes, and at home.