The listening skill seems to be the most difficult among all language skills. This difficulty stems from linguistic and non-linguistic problems i.e. difficulties that accompany the process of teaching and learning listening. This paper aims to investigate the most problematic areas in teaching the listening skill. Two data collection procedures were employed to collect the data for this study; a classroom observation, and a questionnaire for teachers. Fifty teachers of English language responded to the questionnaire and 11 secondary schools in five districts of Aden Governorate were observed for the purpose of collecting data on the teaching of the listening skill. The data were analysed quantitatively and qualitatively.