Previous investigations of the perceptual overshoot effect observed in vowel reduction in vowel-to-vowel transitions have shown that, within certain limits, the perceived vowel at the end of the transition obeys a trade-off rule. This trade-off was manifest in that the vowel target at the endpoint the transition was heard after covering an approximately similar trajectory length, regardless of the vowel context. The present experiments, however, demonstrate that the overshoot is much influenced by the duration of the initial vowel, i.e., by a context that can be heard either as mono- or disyllabic, and that this context also interacts with transition velocity.