Many people in the instructional design community may wonder why AECT should devote a special session during its most recent International Convention in Anaheim, CA, to the issue of ambiguity. Isn't the whole idea behind well designed instruction that it should be ambiguity-free? If a debate on the issue of ambiguity is necessary at all, shouldn't such an exercise simply focus on possible ways to improve instructional design procedures so as to remove ambiguity to the maximum extent possible? Not so, was the idea of a group of people brought together by the Learning Development Institute (LDI - http://www.learndev.org). The group, representing a variety of disciplines and connected in different ways to the practice and theory of cognition, learning, teaching and design, met at a special LDI workshop organized and coordinated in the framework of AECT's 2003 International Convention. The question framing their deliberations was this: "What should one do in the learning environment to prepare people optimally for life in an ambiguous world?" The workshop participants subsequently served on the panel of a special discussion session open to the conference attendees at large. This article highlights some of the concerns that emerged from the Anaheim debate, which involved panelists, discussants and attendees of the special session and may explain why, after all, one should bother about ambiguity.