The problem of understanding, one of the significant topics for the later stage of Wittgenstein's philosophy, replete with appeals to the use of mathematical symbols, caused, as they say, an ambiguous reaction among both mathematicians who took the time to look into them and among the philosophers of mathematics proper. However, the publication in 1982 of S. Kripke's book Wittgenstein on Rules and Individual Language sparked a boom in research centered around Wittgenstein's alleged argument for skepticism. A feature of Kripke's argumentation was the presentation of an arithmetic example, which was linked to the general philosophy of Wittgenstein, whose later philosophy was replete with paradoxical statements like this: even if a mathematician fully understands the definitions and terms in the proof, he may still not believe it. Such statements clearly contradicted mathematical practice, and yet many philosophers were able to link this paradoxicality with the leading theme of Wittgenstein's thinking, namely with the so-called rule-following problem. It is believed that the focus of the later Wittgenstein is on the problem of understanding, in its broadest sense; and, since his skepticism is seen in mathematical examples, it is natural to consider the problem of understanding in the process of mathematical proof. An essential role in the analysis of Wittgenstein's understanding is played by the concept of rule-following and its skeptical interpretation, which problematizes the establishment of the correctness of following a rule. We have Wittgenstein's key recognition that the learning process in a community tends to lead to a tendency for all members to give the same answers, and it is this circumstance that is the criterion for a "correct" answer. In other words, the answers are the same, despite radical conventionalism, because the members of the community are playing the same language game. Another way to express this circumstance is that they all share the same life form. But, at the same time, we do not understand (or do not comprehend) the rule that determines our choice of the "correct" sequence extension according to the concept of a mathematical function. The point is that we share a common concept because we agree in our answers. Working mathematicians are unlikely to agree that they are talking about the same results because they play the same language game. For the most part, working mathematicians share the Platonist view that they discover mathematical objects and mathematical truths. Wittgenstein's anti-Platonist position leads him, from their point of view, to a skeptical conclusion. In fact, Wittgenstein admitted that there is no explanation as to why we tend to agree in our answers. Is not there a certain kind of a tension here between the analysis of Wittgenstein's work in line with the general philosophy of language and its application to mathematical practice? If so, then this important circumstance requires special attention, since a skeptical argument appeals to albeit simple but mathematical examples.