This chapter attempts to analyze how problems are composed in school problem books, which contain hundreds of problems—problems that may be altogether unoriginal, not necessarily beautiful, and not necessarily demand creativity of the solver but which are nonetheless useful for pedagogical aims. In encouraging teachers to teach through and to pose problems, it is desirable to first take a closer look at existing problem books. The present study uses several popular and even famous Russian problem collections for this purpose. Such an analysis makes it possible to identify certain typical techniques as well as contribute to the discussion of certain complex issues, including issues surrounding the notion of a problem’s “difficulty.”