Add the oats, raisins and pumpkin pie spice to the carafe of a blender and pour in the milk, adding more to cover the oats if needed. Stir completely and set aside until the oats are soft, 15 minutes.
Blend on high speed until pureed and smooth, about 1 minute. Add the yogurt, brown sugar and 1 1/2 cups ice, and blend on high speed until smooth, about 30 seconds. Pour into 2 pint glasses.
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