Pail labeling systems are ideal for labeling medium-sized containers such as pails, buckets, large cans in all industries such as food, chemicals, lubricating oils, paints, and varnishes. The containers can be round, conical, oval, rectangular, made of plastic, or metal. The machine automatically orients, lifts the handles to exlude their interfering during labeling process, precisely and accurately applies the labels around the pail using labeling unit with vacuum belting system.