The causes of IS (Information Systems) failure have become increasingly complex. This requires us to be sensitive to how a failure may be situated in the socio-historical context of organizations. This study analyzes how the collapse of organizational learning may be attributed to recurrent IS failures in one particular organization. It suggests that the repeated failed implementations are due to four learning barriers, in terms of the limits of organizational intelligence, disincentive for learning, inappropriate organizational design, and education barriers. These learning dysfunctions may cause organizations to become trapped in permanently failing IS projects. As a result, organizations become entrapped in serial failures when one IS project after another is tried out and then abandoned before enough experience has been accumulated for it to be employed successfully. Therefore, initial failure leads to further search and change, which leads to more failures. This study elaborates the cyclical pattern of IS failure by analyzing the concept of “failure trap”, and suggests ways to break the cycles of IS failure.