Online video advertising continues to play an important role in increasing brand awareness in recent years. This paper aims to develop and test a feasible conceptual framework about how video advertising characteristics and technological interactivity influence target audience’s receptiveness of designated advertising messages and their behavioral intention. A survey was conducted with over 170 valid Internet savvy viewers in Singapore. Using structural equation modeling, the study found that brand recognition was directly influenced by advertising informativeness and technological interactivity. Surprisingly, advertising obtrusiveness was found to have no significant effect on brand recognition. Brand recognition also had direct impact on purchase intention. The theoretical and practical contributions of the study were discussed.