This paper reports on the development and piloting of an adaptive, online placement exam that will be administered to L2 and heritage learners of Spanish at the University of Illinois at Chicago. Particular attention is given to the structure of the exam and the linguistic strategies employed to distinguish heritage speakers from L2 learners. Results obtained from three pilot phases are presented along with a description of modifications made during each stage. Further challenges and steps are outlined. (Contains 10 notes, 11 tables, and 4 figures.)