This paper reports on Wittgenstein’s use of pictures and diagrams undertaken through an analysis of the surrounding co-text in the published works. It is part of a larger project to develop tools for the integrated semantic analysis of images and text in Wittgenstein’s original manuscript and typescript sources. The textual analysis took keywords, phrases and punctuation as possible indicators of definitive samples and rules in propositions and non-propositions. For reasons argued in the paper we focused on non-propositions and differentiated those that functioned descriptively from those that functioned definitively. Finally, from the range of definitive statements we investigated those that functioned according to Wittgenstein’s concept of a rule. In all cases we focused on collocation of indicative text with images. We concluded that Wittgenstein’s practice accorded with his early statements about images needing accompanying words to activate their propositional status, but that images could function independently as non-propositional descriptive or definitive samples. As definitive samples, many images also had the capability to function as rules, or independently as proofs. Since the picture-sentences rely on iconicity to communicate rules that may otherwise he hidden in our language practice, we speculate that the iconic relationship may belong to hinge epistemology. This is proposed as a strand for future research.