The present invention is generally directed to systems and methods for monitoring whether an item is properly delivered to a designated delivery point. According to one aspect of the invention, location data and timestamp data is generated in association with the transport and delivery of an item to a delivery point. The location and timestamp data can be compared, respectively, to at least one predetermined geographic boundary that defines a geographic area encompassing the designated delivery point, and to a scheduled time window within which delivery of the item is to occur. This information can be used to determine if a problem has arisen with regard to the transport and delivery of the item to the delivery point. The system is generally configured to generate one or more alerts if it is determined that a particular item has been transported or delivered in an unauthorized manner.