The hard-to-achieve skill of glass painting is most easily acquired by copying. If a student, unfamiliar with the complexities and possibilities of a new technology, embarks on designing and developing a personal project, failure to meet his or her expectations may discourage any further interest in the subject – at times forever. However, if a student carefully follows an otherwise impeccable example, he or she is then rewarded with a compelling, almost certainly appealing result – the fruits of his or her diligent work. In doing so, an understanding of techniques and skill cultivation are imperceptibly acquired. In the first half of the 2022/2023 academic year, 4th year students of the Sergey Andriaka Academy of Watercolor and Fine Arts were invited to copy portraits by Hans Holbein the Younger (1530s) that were executed in a complex hybrid technique on primed paper of various colors. They were also requested to produce a copy of a self-portrait by Annibale Carracci (1594), drawn with red and white chalk on rose paper. When transferring the drawing into a new material, an attempt was made to accurately convey the nature of the stroke, the texture of the paper, as well as to emulate underdrawing with charcoal, white and red chalk.