Healthcare insurance is a complex financial product with many variables involved. What drives perceived ease of use (PEOU) and perceived usefulness (PU) of healthcare insurance applications (HIAs), be they websites and mobile apps? We propose a communication-driven usefulness hypothesis, which posits three aspects of communication with healthcare insurer providers determining PEOU and PU. Those aspects are: information quality (IQ), interaction ease, and provider competence. The results from 333 survey questionnaires from current healthcare insurance customers support our hypothesis. Thus, future studies should examine further the driving factors of PEOU and PU of the apps involving complex products and services besides healthcare insurance.