An online delivery servicing system includes a server that functions with a customer computing device to obtain delivery confirmation request information associated with an online gift purchased by a customer for a recipient in which the delivery confirmation request information is associated with a quantity of delivery confirmation messages to be transmitted to a recipient of the online gift and a period of elapsed time for each delivery confirmation message. At each period of elapsed time, the server transmits one of the delivery confirmation messages to a recipient computing device associated with the recipient such that, when a response to the one delivery confirmation message is received, the server transmits a customer confirmation message to the customer computing device, and when the quantity of delivery confirmation messages have been transmitted and no response has been received from the recipient computing device, the server transmits a customer delivery failure message to the customer computing device.