A delivery scheduling method includes receiving a bundle request from a user and identifying a first prescription scheduled for delivery within a date range. The method includes setting a scheduled delivery date of the first prescription as a target delivery date, identifying a set of prescriptions scheduled for delivery within a predetermined time of the target delivery date, and selecting one of the set of prescriptions as a candidate prescription. The method includes obtaining prescription parameters of the candidate prescription including a prior fill date of the candidate prescription and determining a required fill date of the candidate prescription. The method includes determining a blackout window for the candidate prescription based on a predetermined window following a prior fill date of the candidate prescription and, in response to the required fill date being after the blackout window, adjusting a delivery date of the candidate prescription to the target delivery date.