We identify and illustrate five important kinds of Dialectical Examples, standard configurations of cases which enable an arguer to justify rhetorical assertions effectively by example. Our computer program generates Argument Contexts, collections of cases that instantiate Dialectical Examples from an on-line database of cases according to a user’s general specifications. The Argument Context generation program provides a human or automated tutor a stock of Dialectical Examples to teach novice advocates (first year law students) how to recognize, carry out and respond to the associated rhetorical moves. Although generating such examples is very hard for humans even when dealing with small numbers of cases, our program generates and organizes such examples quickly and effectively. In a preliminary experiment, we employed program-generated Argument Contexts manually to teach basic argument skills to first year law students with good results. Our ability to define such complex examples declaratively in terms of logical expressions of Loom concepts and relations affords a number of advantages over previous work.