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Power system islanding can improve the continuity of power supply. Synchronous islanded operation enables the islanded system to remain in phase with the main power system while not electrically connected, so avoiding out-of-synchronism re-closure. Specific consideration is required for the multiple-set scenario. In this paper a suitable island management system is proposed, with the emphasis being on maximum island flexibility by allowing passive islanding transitions to occur, facilitated by intelligent control. These transitions include: island detection, identification, fragmentation, merging and return-to-mains. It can be challenging to detect these transitions while maintaining synchronous islanded operation. The performance of this control system in the presence of a variable wind power in-feed is also examined. A Mathworks SimPowerSystems simulation is used to investigate the performance of the island management system. The benefit and requirements for energy storage, communications and distribution system protection for this application are considered.