An authentication challenge system for performing secondary authentication for an account associated with an online store is described. In one embodiment, the authentication challenge system includes a question generation engine, which can derive a series of questions based upon activity associated with a user account of an online store; a network interface, which can transport the series of one or more questions derived by the question generation engine to authenticate the user to the online store; a confidence engine, which can determine a required confidence level for a successful authentication, and can compute a confidence score of the user identity; and a quality engine, which can adjust the question generation engine and the confidence engine based upon an analysis of question and answer metrics across multiple accounts of the online store. The online store can include digital media, such as music, movies, books or applications for electronic computing devices.