Facing the demands of the pandemic and distance learning, English learners require educational technologies that are accessible, engaging, and effective. Meeting these demands requires educational technology developers to consider learners’ sociocultural contexts. Learning theories can be applied to meet individuals’ needs to optimize chances for participation, engagement, and learning gains. This article describes two Internet-based digital technologies that target struggling adult readers who need to improve their comprehension skills: SARA (Study Aid and Reading Assessment) and AutoTutor for Adult Reading Comprehension. The SARA assessment provides a diagnostic profile for individuals’ reading strengths and weaknesses. This profile can be used to guide the selection of reading comprehension lessons in AutoTutor-ARC, a digital technology that both adapts to learners’ performances and engages them in an immersive learning experience using a three-way conversation with computer agents acting as a tutor and a peer to discuss texts. We discuss how these technologies can be integrated into educational settings to improve engagement and learning.