Successful software engineering requires experience and acknowledgment of complexity, including that which leads designers to recognize ambiguity within the software design description itself. We report on a study of 21 post-secondary institutions from the USA, UK, Sweden, and New Zealand. First competency and graduating students as well as educators were asked to perform a software design task. We found that as students go from first competency to graduating seniors they tend to recognize ambiguities in under-specified problems. Additionally, participants who recognized ambiguity addressed more requirements of the design.