A method of custom labeling products in which users specify, via a purchasing interface, product label images in correspondence with products. A label group is generated for each of the users. The label group includes an indicator label image providing a purchase identifier and product identifiers, and the product label images arranged in a sequence specified by the product identifiers. The label groups are printed to produce printed label groups. The printed label groups are transferred to a labeling machine. A conveyor system is controlled to release, for each of the printed label groups, the sequence of the products specified by the product identifiers. Printed product labels of each of the printed label groups are applied to the corresponding sequence of the products.