Time to stabilization (TTS) has been introduced as a method to analyze dynamic postural stability during jump and landing tasks, but has also been applied during the transition task from double-leg stance (DLS) to single-leg stance (SLS). However, the application of the originally described TTS technique during the latter task has some important limitations. The first goal of this study was to present an adapted version of the TTS technique to provide an effective alternative method to better analyze postural stability during the transition from DLS to SLS. The second goal was to study the influence of pathology and different speeds on postural stability outcomes. Fifteen healthy control subjects and 15 subjects with chronic ankle instability (CAI) performed the transition task on their preferred speed and as fast as possible, with eyes open and with eyes closed. Subjects with CAI performed the transition significantly slower when moving at their preferred speed with eyes closed. The time subjects needed to reach a new stability point was not discriminative between groups and largely dependent on movement speed. However, the amount of sway after this new stability point was significantly increased in the CAI group and when eyes were closed. The results of this study suggest that subjects with CAI have a decreased ability to overcome the postural perturbation created by the voluntary movement from DLS to SLS. Focusing only on TTS during the transition from DLS to SLS may lead at least in some cases to misinterpretations when assessing postural stability.