This paper discusses the peculiarities and problems of teaching the historical aspects of Information Security Science (ISS) to the students of the “Information Security” specialization. Preferential attention is given to the ISS area with the longest history, namely cryptography. We trace exactly what ideas of fundamental importance for modern cryptography were formed in each of the historical periods, how these ideas can help students in mastering the training courses’ material, and how to communicate these ideas to students in the best way. The conclusions are based on the results of studies conducted over a few years at the “Cybernetics and Information Security” Faculty of the NRNU MEPhI, where our ideas are implemented in the educational process. We teach the history of cryptography in a few educational courses for Specialists in IS and Masters in Business Continuity and IS Maintenance in the form of introductory and individual lectures and seminars. Specific recommendations on the use of the historical facts considered during the classes are given.