A system and method for enhancing digitally informed delivery of delivery items such as mail. The sender of a delivery item creates custom electronic text, files, images, web pages, or other electronic/digital resource(s) to provide to the recipient. A postage meter, a server of the delivery service, or the like creates a digital indicia that includes the digital resource, associating it with the delivery item. When the delivery item is processed by the delivery service equipment during transit, the digital indicia is read and the associated digital resource is are identified therefrom. The delivery service equipment transmits, to the delivery item recipient, an electronic notification indicating that the delivery item is en-route to the recipient, and also provides the associated digital resource. The recipient can then access the resource, e.g., the custom text, files, images or web pages associated with the delivery item.