By the age of 1 year toddlers demonstrate distinct coping habits for dealing with frustration. However, these habits may be open to change and reorganization at subsequent developmental junctures. We investigated change in coping habits at 18-20 months, a normative age for major advances in social cognition, focusing on the dynamic systems principles of fluctuation and novelty at transitions. Specifically, we asked whether month-to-month fluctuation, novel behavioral habits and real-time variability increased at the age of a normative transition, despite individual differences in the content of behavior. Infants were given frustrating toys while their mothers sat nearby without helping, on monthly visits at 14-25 months (before, during and after the hypothesized transition). State space grids representing patterns of behavioral durations were constructed for each episode and compared over age. As predicted, month-to-month fluctuation in grid patterns increased temporarily between 17 and 20 months, partly independently of a concurrent peak in distress, and new behavioral habits replaced old ones at the same age. Coping habits changed differently for high- and low-distressed toddlers. However, changes in real-time variability did not generally meet our expectations.