This paper is a contribution to the understanding and management of Open Source Software (OSS), in discussing the issues of license choice and how to match this to organisational aims, in the adoption and usage of Open Source Software. License choice governs the obligations of an organisation for their software. The paper describes which issues in an OSS license which are applicable to any OSS license, thereby being generic or de jure issues, and those which are outcome issues, allowing for the fulfilment of organisational objectives, either from the licensor or licensee perspective.