To identify how contextual usage frequency and lexical frequency interact when controlling for traditional linguistic constraints, this study analyzes the effect of frequency on (ING), taking into account a word's frequent context of occurrence. The data consist of 13,167 tokens of (ING) from interviews with 132 speakers conducted in Raleigh, North Carolina. Results from mixed-effect logistic regression show a strong effect of frequency on the realization of (ING), and this effect interacts with phonological context of occurrence. Frequent occurrence in environments that favor -in amplify the effect of lexical frequency; conversely, frequent occurrence in environments that favor –ing dampen the effect of overall frequency. Frequency also interacts with year of birth, showing an entrenchment of high-frequency words, lagging behind the community change toward the –ing variant in apparent time. Overall, these findings support the usage-based position of frequency effects as the result of a dynamic interplay between context of use and cognitive systems.