An apparatus and method for assisting medication are disclosed. The apparatus includes a medication box and a medication service device. The medication box includes a plurality of containers each storing a paper bag of medication, and discharges a paper bag of medication from a corresponding one of the containers using a rotational force of an electric motor, and detects whether the stored paper bag of medication is present or is discharged. The medication service device includes a situation detector detecting a status of a user based on user identification and signal strength included in a radio frequency signal, and a status of the medication box, a situation recognizer recognizing a medication situation, and a service executor generating a service for medication. The user who has to regularly take a paper bag of medication for a long time can be assisted to take an accurate dose of medication on time.