In this paper we present an analysis of top security issues related to IT outsourcing. Identification of top issues is important since there is a limited understanding of security in outsourcing relationships. Such an analysis will help decision makers in appropriate strategic planning for secure outsourcing. Our analysis is conducted through a two-phase approach. First, a Delphi study is undertaken to identify the top issues. Second, an intensive study of phase one results is undertaken to better understand the reasons for the different perceptions.