This dissertation consists of three separate essays, all of which use structural and econometric approach to investigate consumers' decision-making processes in the context of an online continuous subscription service industry. The first essay explores why consumers over-purchase relative to their observed consumption rates; and consumers' risk aversion and learning influence their choices over service plans over time. The second essay taps the dynamics of the consumers' underlying preferences for the company's key service components such as price and service quality. The third essay examines the relation between consumers' decisions to stay with the company and their decisions to accept the win-back plan offered by the company. Based on the insights into the consumers' decision calculus, this dissertation is able to provide recommendations on the company's various strategies including product design, dynamic product offering and customer win-back.