As planners and decision-makers experiment with information and communication technologies (ICTs), it’s important to explore and analyze these attempts in different planning systems and contexts. The aim of the article is to compare the use of and aspirations attached to e-planning in Helsinki, Finland and Sydney, Australia. This comparison will highlight the interrelationship between planning context and its amenability to an e-planning approach and shows there are shared themes in both cases: firstly, the complexity involved in reconciling the aims of the e-planning experiments and their connection to the planning process itself (roles, objectives, implementation of tools and processes). Secondly, the way that e-planning opens up cracks in the façade of administration, and thirdly, the ways in which e-planning provides possibilities to reshape existing planning procedures. The authors argue that the different planning and governance contexts affect the adoption of e-planning and this adoption is necessarily a selective process.