A labeling assembly for applying labels carried on a substrate to a sequential series of moving documents is provided. The assembly transports the document in a generally vertical end on end orientation down a conveying path and peels the label from the substrate to position the peeled label in a generally vertical orientation. The labeling assembly also includes a paddle having a front surface with vacuum ports for attaching and releasably retaining the peeled label on the front surface. An actuating mechanism pivots the paddle to force an end of the retained label into contact with the document. Upon contact, the downstream end of the retained label adheres to the document and the label is pulled off the paddle. As the label is pulled off the paddle the contact between the end of the paddle presses the label against the document.