This study sought to determine the relationship among student- and task-level variables at play in the digital storybook listening experiences of 130 English-speaking preschoolers at risk of reading failure. Specifically, this study investigated the relationship among the (1) features of computer-based electronic storybooks, (2) preschoolers' competency in the task environment, and (3) preschoolers' background knowledge with respect to listening comprehension outcomes following a single digital storybook listening experience. The results indicate significant and strong relationships among the three variables under investigation and their consequent understanding of the digital storybook (i.e. explicit and implicit/inferential content related to the plot). The preschoolers' topic knowledge was the best predictor of comprehension. In addition, the interaction between the features of the e-book and the preschoolers' competency in the task environment also significantly predicted the outcome.