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Many countries have declared future renewable energy penetration targets. Wind power connection to power systems is delayed by limited transmission system capacity as attractive wind sites are often located in weakly designed transmission areas. Optimal use of existing transmission system resources should be made in the allocation of capacity connection permits. The volume of wind power connection applications and their power production statistical inter-dependencies suggest that they should be assessed in a collective probabilistic manner. This paper uses a sequential probabilistic load flow method in tandem with a linear programming computational geometry constraint redundancy approach to optimally allocate wind capacities given the transmission system capacity that is securely available.