Organizations that have come to depend on legacy systems face quite a paradoxical problem. Maintaining the system might prove ineffective in accommodating necessary changes, but a system migration project is expensive and incurs a high amount of risk. Organizations are therefore hesitant to respond to the legacy system problem by undertaking action. Legacy system are often not causing their organization any problems at present, but a focus on the future with regard to the legacy system problem is lacking. This results in IT systems reaching an end-of-life state. The research therefore set out to explore a future-oriented perspective on legacy systems by means of observation, a literature review and a survey. The researcher found the key concept of a future-oriented perspective to be that any system that is limiting an organization to grow and innovate can be regarded as a legacy system. A framework to designate legacy status to IT systems is proposed in order to guide practitioners to acknowledge a problematic IT system to facilitate appropriate response at the right time. In relation to a future-oriented perspective, when to designate legacy status is best determined according to the system’s flexibility towards change and the alignment of the system with the business. In that regard, IT systems are end-of-life systems when they are too inflexible to change, and as a result become unaligned with either current operations or a future business opportunity or need.