The paper presents the results of investigations into the technological possibilities of controlling the transgalactosylation process of lactose in permeate after whey ultrafiltration in order to improve the efficiency of galactooligosaccharides or lactulose synthesis. The synthesis efficiency was influenced by the selection of a β-galactosidase preparation, substrate concentration and, in the synthesis of lactulose, also by the ratio of lactose and fructose added to the reaction mixture. The obtained synthesis efficiency of GOS and, most of all, of lactulose (65 g L−1), may be found satisfactory. The study also resulted in a proposed GOS or lactulose concentrates (concentrated or dried) production technology using permeate after ultrafiltration of milk or whey as lactose sources.