In the evolving dialogue concerning "gatekeeper" duties of corporate lawyers, the scope and social utility of the attorney-client privilege in the corporate setting and related concepts of client confidentiality have come under increasing scrutiny. Indeed, in the face of growing pressure on corporations to waive the privilege in connection with government investigations, some have questioned whether there is any legal or social justification for the corporate attorney-client privilege. While these challenges play out most directly in the litigation setting, concepts of privilege and confidentiality may also significantly affect the nature and flow of communications necessary for corporate and transactional lawyers, including in-house lawyers, to provide effective and appropriate counsel to their clients. This article suggests that current initiatives that weaken the practical vitality of the privilege in the corporate setting do not take into account the realities of attorney-client communications in that setting, and that such efforts may undercut the effectiveness of corporate and transactional lawyers in promoting legal compliance by their corporate clients. The article further suggests that the lessons of Upjohn Company v. United States concerning the importance of the corporate attorney-client privilege have become obscured in the wake of recent corporate scandals and that those lessons should inform the current debate.