We examined the extent to which the timing of inferential questioning influenced kindergartners' inferencing performance in a non-reading context, while also taking into account individual differences in language comprehension and executive function. Students completed the eight-week Early Language Comprehension Individualized Instruction (ELCII) application by responding to audiovisual inferential questions administered in one of two timing conditions: either (1) during video watching at various points (online) or (2) after the video was finished ("offline"). Results suggest that online questioning fostered greater overall gains in inferencing skill from pretest to posttest. Moreover, students with higher executive function demonstrated greater gain in inferencing than students with lower executive function. Likewise, students with higher language comprehension skills demonstrated greater gains in inferencing than students with lower language comprehension skills. Theoretical and instructional implications of the findings and areas for future research are discussed. [This is the online version of an article published in "Scientific Studies of Reading."]