The advent of outsourcing in e-Security raises a series of management issues in the selection, implementation and evaluation of available solutions. More broadly, the growth of electronic commerce has increased business awareness of the need to respond to e- Security and other related issues. To date, there has been a lack of Australian research in this area and limited evidence suggesting that Australian medium-sized organisations are coherently managing the challenges faced. This paper examines key management issues facing medium sized organisations in e- Security, explores different outsourcing models and provides a generic four-step approach to assist them in making strategic security decisions.