A bolus of 0.125% bupivacaine (8ml) was given for post-operative analgesia with considerable resistance. It was immediately followed by hemodynamic deterioration along with fall in sensorium. After resuscitation, CT brain revealed pneumoencephalus around the brainstem. The higher force generated during injection could have injured epidural venous plexus and air inadvertently entered the veins. The source of air could have been from the epidural catheter or injection syringe. Hence it is suggested that position and patency of the epidural catheter must be checked each time before administration of injections especially after position changes. On presence of slightest resistance, injections should be withheld till the cause is ascertained by a trained personnel.