<![CDATA[The increasing integration of Artificial Intelligence (AI) and digital technologies into language education has created new opportunities to improve Arabic listening instruction (maharah al-istima'). However, educators continue to face challenges in selecting digital learning media that best align with specific pedagogical objectives. This study comparatively examines the pedagogical characteristics of three AI-assisted learning applications—Spotify, Voicemaker, and Quizalize—to identify their respective contributions to maharah al-istima' instruction. A qualitative comparative research design was employed using systematic observation and document analysis. Data were analyzed through the Paired Comparison technique based on the six quality characteristics of the ISO 9126 model: Functionality, Reliability, Usability, Efficiency, Maintainability, and Portability. The findings indicate that each application performs distinct yet complementary instructional functions. Spotify is most effective in providing authentic listening exposure through podcast-based learning, Voicemaker excels in producing adaptive AI-generated audio for customized instructional materials, while Quizalize strengthens formative assessment through interactive quizzes, immediate feedback, and gamification. Rather than functioning as competing technologies, the three applications collectively represent complementary stages of Arabic listening instruction encompassing authentic input, controlled practice, and interactive evaluation. This study contributes a comparative pedagogical framework for selecting and integrating AI-assisted digital learning media, providing practical guidance for educators to design more adaptive, evidence-based, and learner-centered maharah al-istima' instruction.]]>
