Medication discrepancies can place patients at increased risk for adverse drug events. We sought to determine the frequency, type, and reason for medication discrepancies in patients receiving home healthcare following hospital discharge. We conducted a retrospective, observational study of adults discharged from an academic medical center who received home healthcare following hospital discharge from one affiliated home healthcare agency. Medication discrepancies were identified by comparing the hospital discharge medication list to what the patient was taking at the first home healthcare visit. Almost all patients (66/70, 94%) had at least one medication discrepancy. The median number of discrepancies per patient was 5. Nearly half of the discrepancies were omissions (46%), in which the patient was not taking a medication on the discharge medication list. Increased age was significantly associated with fewer medication discrepancies overall (IRR = 0.99, p < 0.05). Higher health literacy was associated with more omissions (IRR = 1.85, p < 0.05).