This paper explores the semiotics of Charles Peirce in relation to Colin Koopman's advocacy for a new wave of pragmatism, which he terms transitionalism. Presenting both similarities and differences between these two, the main point is that Peirce's semiotics fits the general idea of a transitionalist, as contrasted to substantialist, philosophy, even though Koopman explicitly excludes this possibility. This is argued both on the grounds of Peirce's own writings and in view of recent, post-Peircean developments, particularly in semiotics, which highlight certain possibilities of Peirce's pragmatism. Overall, Peirce's concept of the sign as the tool of a relational logic that explicates the transition from hypothesis to conclusion recommends Peirce's pragmatism as avant-garde for its time and justifies its labelling as transitionalist pragmatism. Some implications for education are identified along the development of the argument.