As theorized in Anderson's (1983, 1995) associative stage of skill acquisition, errors or obstacles become an important index of the learning process. However, learning obstacles have not been widely researched in the field of language learning strategies. This study explores the difficulties or barriers confronted by the EFL (English as a Foreign Language) learners while acquiring listening comprehension strategies during a training program. The findings indicate that the obstacles confronted by the learners are multifaceted. Each facet carries a probable risk of comprehension failure. Learning barriers are associated with the internal factors of learners such as their affective statuses, listening habits, information processing capacities, English proficiencies, and their belief about listening activities. Other barriers concerned the nature of listening strategies and the listening material used. Based on the findings, a series of pedagogical implications are provided.