Transparency is widely recognized as indispensable to privacy protection. However, producing transparency for end-users is often antithetical to a variety of other technical, business, and regulatory interests. These conflicts create obstacles which stand in the way of developing tools which provide meaningful privacy protections or from having such tools adopted in widespread fashion. In this paper, we develop a «map» of these common obstacles to transparency, in order to assist privacy engineers in successfully navigating them. Furthermore, we argue that some of these obstacles can be successfully avoided by distinguishing between two different nonceptions of transparency and considering which is at stake in a given case-transparency as providing users with insight into what information about them is collected and how it is processed (what we call transparency as a «view under-the-hood») and transparency as providing users with facility in navigating the risks and benefits of using particular technologies.