The article discusses the issues of mathematical understanding as an educational practice of identifying the algorithmic meanings of mathematical (mathematized) educational texts. The hermeneutic orientation towards following the “guiding thread of language” (G.-G. Gadamer), as it is shown, cannot be narrowed to the attitude towards natural languages inherent in humanitarian educational practices. The “common place” of mathematical understanding in educational practices is: some of created languages (of scientific communication) being consolidated around the mathematical installation are not reducible to its sign universality or educational generalizations. But it often turns out to be outside the field of view of practicing teachers, in a didactically abstract position. The article substantiates the possibility of rehabilitating the hermeneutic attitude in mathematical education in connection with its development and strengthening in understanding the prerequisites for the algorithmic solution of mathematical problems (the need for additional information, non-standard solution techniques, transfer of educational goal setting to the area of interdisciplinary relationships or life experience, etc.). The author shows and comments on the effectiveness of the hermeneutic approach in mathematics education using examples of solving problems in algebra, geometry and in constructing mathematical models of various physical processes.