Instruction in Arabic listening skills (maharah istima') within pesantren (Islamic boarding school) settings faces various challenges particularly students' limited ability to comprehend vocabulary, recognize Arabic phonemes, and grasp the meaning of conversations necessitating innovations in digital technology-based learning. This study aims to analyze the impact of using the Teach Me Arabic application on improving students' listening skills at the Bustanul Lughah Al-Arabiyah Institute, Miftahul Ulum Islamic Boarding School in Sidomukti, Mayang, Jember. A quantitative method with a pre-experimental design (one-group pretest-posttest) was employed, involving 45 students selected via total sampling. Data were collected through pre-tests and post-tests that met validity and reliability standards, then analyzed using descriptive statistics, a paired-sample t-test, N-Gain, and Cohen's d effect size. The results show that the students' average score rose from 54.6 in the pre-test to 61.2 in the post-test, a difference of 6.6 points. Hypothesis testing revealed a calculated t-value of 4.43, exceeding the t-table value of 2.02 at a 0.05 significance level, thereby confirming a significant impact of the Teach Me Arabic application on the improvement of students' listening skills. The N-Gain score of 0.14 indicates an improvement in the low category, while the effect size (Cohen's d) of 0.65 falls into the medium category, demonstrating a practical impact on learning outcomes. The findings indicate that the Teach Me Arabic application is effective as a supporting medium for Arabic listening instruction; however, its effectiveness would be optimized if combined with teacher guidance through a blended learning approach. This study offers implications for the development of digital technology based Arabic language instruction within pesantren environments.