Drawing mainly from the Tractatus Logico-Philosophicus and his middle period writings, strategic issues and problems arising from Wittgenstein’s philosophy of mathematics are discussed. Topics have been so chosen as to assist mediation between the perspective of philosophers and that of mathematicians on their developing discipline. There is consideration of rules within arithmetic and geometry and Wittgenstein’s distinctive approach to number systems whether elementary or transfinite. Examples are presented to illuminate the relation between the meaning of an arithmetical generalisation or theorem (...) and its proof. An attempt is made to meet directly some of Wittgenstein’s critical comments on the mathematical treatment of infinity and irrational numbers. (shrink)