Blend 2 cups milk, sugar, pudding mix, rum-flavored extract, nutmeg, allspice, and ginger in a blender on medium-high speed until smooth; pour into a pitcher. Stir remaining 3 cups milk into mixture. Refrigerate eggnog until thickened, at least 1 hour. Stir well before serving.
Sprinkle a little cinnamon on top for garnish and extra flavor.
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