While developing and maintaining a connection between a brand and a customer has always been in the forefront of marketers' agendas, it has become an even more pressing goal as digital trends in marketing surface. Although the idea of using rewards to foster consumer-brand connection has been around for decades, marketers are still struggling to optimize the benefits. How can marketers use rewards to better connect with their customers? Are there certain types of rewards that are more effective than others? Are certain rewards more effective when being implemented under brands of a certain personality type? In a society that values connection and relationship, marketers cannot lose their ability to appreciate customers under digital constraints and to marketplace competition. Through a field study and scenario-based experiment, we explore how and why low conditional vs. high conditional rewards influence consumer-brand connection and the role brand personality plays.