Inclusion Criteria:
* Age ≥ 25 years
* History of solid organ (not hematologic) cancer diagnosis (except patients with central nervous system \[CNS\] cancer who have history of seizures or untreated brain metastasis). Patients may be either in remission or have active disease. Patients must be considered medically fit by their treating physician to participate in the study
* Eastern Cooperative Oncology Group (ECOG) performance status (PS) 0, 1 or 2
* History of insomnia for which the patient would like an intervention
* Insomnia Severity Index Score ≥ 15. Patients can answer questions orally rather than completing worksheet, for screening only
* Willing to abstain from alcohol, anticholinergics, and benzodiazepines while on study
* If on opioids, must be a stable dose ≥ 30 days prior to randomization (no changes to prescriptions, this can include as needed \[PRN\] dosing) with no plans to increase during the study period
* White blood cell count (WBC) ≥ 3,000/mm\^3 (obtained ≤ 30 days prior to randomization)
* Hemoglobin ≥ 8 g/dL (obtained ≤ 30 days prior to randomization)
* Platelet count ≥ 50,000/mm\^3 (obtained ≤ 30 days prior to randomization)
* Alanine aminotransferase (ALT) or aspartate transaminase (AST) ≤ 3 x upper limit of normal (ULN) (obtained ≤ 30 days prior to randomization)
* Glomerular filtration rate (GFR) \> 20 (obtained ≤ 30 days prior to randomization)
* Total bilirubin ≤ 1.5 x ULN (obtained ≤ 30 days prior to randomization)
* Negative pregnancy test done ≤ 7 days prior to registration, for persons of childbearing potential only
* Provide informed consent
* Ability to complete questionnaires and diary by themselves or with assistance
* Willingness to wear a home EEG monitor and have a blue-tooth device for recording (Smart phone, iPad)
* Normal urine toxicology screen ≤ 7 days prior to randomization (abstinence from cannabinoids and other common drugs of abuse: cocaine, benzodiazepines, and methamphetamines)
Exclusion Criteria:
* Any of the following because this study involves an investigational agent whose genotoxic, mutagenic, and teratogenic effects on the developing fetus and newborn are unknown:
* Pregnant persons
* Nursing persons
* Persons of childbearing potential or are able to father a child who are unwilling to employ adequate contraception (e.g., hormonal methods, barrier methods, intrauterine device, abstinence) during the study and for 14 days after their last dose
* Currently using any other pharmacologic agents, over the counter medications or supplements to specifically treat insomnia for ≤ 7 days prior to randomization
* Known primary sleep disorder (restless leg syndrome \[RLS\], uncontrolled apnea, narcolepsy)
* Cannabis use ≤ 30 days prior to randomization
* Active cardiac disease (symptomatic congestive heart failure \[CHF\], arrhythmias, untreated coronary artery disease \[CAD\])
* On warfarin, topiramate, clobazam, or other high-risk CYP3A4 substrates (amiodarone, macrolides, verapamil, fluoxetine, clotrimazole, ketoconazole) per pharmacy review
* History of Human Papilloma Virus positive (HPV+) head and neck cancer
* Any concomitant medications that, in the judgment of the treating physician or pharmacist, could result in an adverse drug effect (increase in substrate level); pharmacy e-consult will be conducted for each patient to determine CYP interactions
* Patients with a history of psychotic disorders (including but not limited to schizophrenia, major depression with psychotic features, brief psychotic disorder). Patients with depression, manic/depression, or obsessive compulsive disorder (OCD) will need clearance from their mental health provider that these medical conditions are controlled and that the patient is appropriate for the study
* Any known hypersensitivity to cannabis
* Patients with CNS cancer or brain metastasis who have had or have seizures
* History of, or current substance use disorder
* Patients with electrocardiography (ECG) test with corrected QT interval (QTc) ≥ 450 msec for men and ≥ 470 msec for women
* Current or past suicidal ideation or suicidal behavior within the last year, as assessed with the Columbia-Suicide Severity Rating Scale (C-SSRS)
* Patients with history off falls in the past 6 months, or considered at risk for falling
