The JESSICA initiative has been set up to respond to development needs of urban areas, which are of key importance for stimulation of sustainable economic growth. It is supposed to provide a more efficient alternative to the traditional EU grants for the implementation of developmental projects. The funding available under the JESSICA framework relies on a repayable and recyclable basis. This means that it not only offers revolving funds, increasing financing capacity of EU cohesion policy, but also creates scope for cooperation between public authorities, financial institutions, and private investors to support implementation of this policy. Since JESSICA supports projects being part of an integrated plan for sustainable urban development, its primary challenge is to combine the objectives focused on urban sustainability and policy intervention with revolving financial models that assume, in principle, the long-term viability of projects. However, taking into particular consideration the needs of urban areas and the EU cohesion policy objective on the one hand, and the organisation and operation of financing engineering instruments on the other, JESSICA seems to be a very ambitious undertaking. The evaluations carried out, up to now, have been mainly focused on its legal and institutional framework, or limited to some selected project. Our study concerns the assessment of all projects implemented within the framework of the JESSICA initiative in five Polish regions, namely: Pomorskie, Mazowieckie, Śląskie, Wielkopolskie and Zachodniopomorskie, in the years between 2007-2015. To do so, we designed a methodological approach for assessing the extent to which projects implemented under the JESSICA initiative have contributed to achieving its fundamental assumptions. Subsequently, we made an assessment of the results of JESSICA through the conceptual lens of sustainable urban development. The main findings show that the range of achieving the assumptions of the JESSICA funding model by projects diverges widely. Many projects were quite well adjusted to the requirements but there were also projects that fulfilled them to a very limited extent.