‘Digital Strategy’ is an EU-level policy promoting the use of ICT in houses and companies across Europe, so as to improve standards of living and competitiveness respectively. This article presents a web Information System which forecasts the potential success of such policies at country and regional level. The proposed system provides guidance for judgmental forecasting processes, incorporating three widely used judgmental approaches, while presenting relevant statistical analysis and qualitative information. A two-way evaluation of the system is also presented. The study concludes with useful comments and avenues for further research.