Organizations struggle to comply with legal requirements as well as customers' calls for better data protection. Yet, information privacy depends on system engineers putting effort into the matter. We interviewed six seniors in system engineering, who work for globally leading IT corporations and research institutions in order to investigate their motivation and ability to comply with privacy expectations. The results of our in-depth interview study point to a lack of perceived responsibility, control and autonomy and to a struggle with the legal world. The information society may be facing the dilemma of asking engineers to live up to a challenge they are currently not ready to embrace.