The main purpose of the present investigation was to explore the effects of a newly-developed educational technology, COMPRENDE, on adolescents' (N = 85) reading comprehension. More specifically, we explored whether exposure to COMPRENDE significantly improved students' reading comprehension performance gains as measured by "Lectum" (a standardized reading test), and to what degree this was effective on struggling readers when compared to proficient readers. Further, we sought to better understand whether planning, monitoring, and evaluation (as metacognitive skills), bridging strategy, contextual vocabulary, perception of COMPRENDE, confidence judgments for performance judged to be correct, and confidence judgments for performance judged to be incorrect (as cognitive skills) significantly predicted reading comprehension performance. Confidence judgments were collected as indices of feeling of knowing (FOKs). Results revealed that COMPRENDE was successful at improving reading comprehension performance but only for struggling readers, and that bridging strategy was the best predictor of reading comprehension performance across both local (item-by-item) and global (holistic) FOKs. Implications for educational practice, technology use in the classroom, research, and theory are discussed.