Previous research established that online shopping activity might be caused by impulse as much as by rational thinking about the conveniences of e-commerce. Interactive features of ecommerce sites, such as email alerts of special offers and “clickable” product arrays, may stimulate unregulated buying activity by undermining consumer self-regulation, but this connection has not been empirically verified. In this study, structural equation modeling techniques were used to model the relationship of interactive e-commerce features to online buying activity with a sample of 174 college students. Recreational shopping orientation predicted the usage of interactive shopping features thought to promote unregulated purchases, increasing deficient self-regulation, and leading to increased online buying activity. Convenience shopping orientation had a direct impact on buying activity, but it did not influence buying activity through the usage of convenience shopping features. Convenience shopping orientation also contributed to the usage of recreational shopping features that promoted deficient self-regulation. Overall, the model explained fifty percent of the variance in online buying activity.