The Kaliningrad region is developing in complicated exclave conditions, which results in insufficient resilience of its economy to external impacts. There is a need for constant monitoring of the economic situation in the region and the adaptation of the regional strategy to changing conditions. This article sets out to evaluate the stages of regional economy development and the methods of its modernisation and restructuring in view of accumulated experience in reacting to changes in conditions of regional development. The authors analyse complex statistical data from 1990—2012 and the modern condition of the Kaliningrad regional economy compared to the national average. The article relies heavily on the results of the survey of specialists working in regional companies. Russian accession to the WTO and the abolition of certain customs privileges planned for 2016 form the basis for the import substitution manufacturing and will significantly affect the conditions of regional economy development. Implementation of the Strategy for the Socioeconomic Development of the Region will contribute to the innovativeness of economy, its export orientation, development through an increase in labour productivity, and cooperation with both Russian and international partners. It will reduce the dependence of production on imported raw materials and semi-finished produces, as well as its energy intensity. The formation of a new more stable economy will be facilitated through federal support and implementation of a number of regional programmes.