Computer program products, methods, systems, apparatus, and computing entities are provided for optimizing package delivery and confirmation are disclosed. In one embodiment, the system's processors accesses a first image of an assigned delivery location captured by a first computing device. The first image comprises an annotation indicating a specific location at the assigned delivery location for delivery of a parcel. At a display device of a second computing device, a real-time image stream comprising the annotation is captured by a camera of the second computing device is displayed. The annotation is overlaid within the real-time image stream based on comparing the first image received from the first computing device to the real-time image stream. The system further captures, from the real-time image stream, a second image when the parcel is positioned at the specific location based on the annotation overlaid within the real-time image stream.