The introductory part of the paper analyzes the increase of a new digital generation of students characterized by freedom, speed, and flexibility (Prensky, 2005; Berk, 2009; Tapscott 2011) optimism, team and global orientation, rationality, extreme curiosity (Jones & Shao, 2011) performance of parallel processes, enjoyment current pleasures, and aspiration for networking (Berk, 2009; Tapscott, 2011). In line with the above, this research aims to determine the advantages and limitations of complex evaluation in the digital environment. A theoretical analysis of the advantages and disadvantages of computer utilisation in the complex evaluation was performed, with special reference to specific aspects (objectivity, individualization, reliability, evaluation of results, processes, and application of knowledge). The attitudes of final-year students of the Faculty of Teacher Education at the University of Belgrade were investigated. The phenomenon of depersonalisation of education was noticed and the advantages and limitations of the use of evaluation in the digital environment were pointed out. Pedagogical recommendations have been made aimed at: 1. the criteria that technology needs to meet in order to support complex evaluation; 2. development of a digitally competent teacher, who is qualified for the pedagogical use of technologies.