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Keen interest in the development and utilization of wind-based distributed generation (DG) has been currently observed worldwide. The reliability impact of this highly variable energy source is an important aspect that needs to be assessed as wind power penetration becomes increasingly significant. Distribution system adequacy assessment including wind-based DG units during different modes of operation is described in this paper. Monte Carlo simulation (MCS) and analytical technique are used in this work with a new implementation of the islanding mode of operation in the assessment. The results show that there is no significant difference between the outcomes of the two proposed techniques; however, MCS requires much longer computational time. Moreover, the effect of islanding appears in the improvement of the loss of load expectation (LOLE) and loss of energy expectation (LOEE).