New technology and access to renewable energy sources enable production of electricity by new actors on the energy markets. One such actor is the energy islands, isolated communities that produce and consume a part or all their energy needs. The E-LAND project is developing a toolbox that use consumers data and external data (weather, energy prices) to deliver an optimal energy schedule, that minimizes the cost of energy production and consumption. The E-LAND solution should support the energy islands to emerge on the energy market using a new technology, with new functionalities, and new ways of thinking performing both their operational and business processes: these changes come with new risks. This paper presents how risks are understood and managed, firstly by the project with regards to the pilot sites, that constitutes a set of first users chosen to represent different industries and energy technologies; and secondly, by the pilot sites themselves. The analysis identified risks with a top-down approach, based on different use cases, designed for each pilot sites. This article is focusing on the development of the risk at the half-way to completion of the project, and the accuracy of the risks seen for the pilot sites as the toolbox is being installed and tested.