Cuff inflation assembly failure can cause problem at the time of intubation, during surgery or at the time of extubation. Incomplete inflation of the endotracheal tube cuff or complete failure to inflate the cuff can cause difficulty in ventilating the patient. Similarly incomplete deflation can lead to vocal cord trauma which can lead to edema of the vocal cords. Therefore, cuff inflation assembly pre–check becomes necessary to prevent such complications. But sometimes kinking of the inflation line due to various reasons may occur leading to difficulty in inflating or deflating the endotracheal tube cuff. We present a case of difficult extubation due to unanticipated cuff inflation assembly malfunction as a consequence of kinking of inflation line under the endotracheal tube fixation.