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Combine brown sugar, water, cranberries, ginger, orange zest, cinnamon, anise in a small pot. Bring to a simmer over medium for about 10 minutes until the cranberries burst. Give them a little mash.
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Pour the syrup through a mesh strainer into a large measuring cup. Allow to cool completely before transferring to a jar with a lid.
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To make the margaritas, add cooled syrup, tequila, and margarita mix to a small pitcher. Stir to combine.
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Add ice to two glasses. Pour half the mixture into one glass and half into another.
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Garnish with limes, orange slices, orange zest, cinnamon sticks, star anise, and fresh cranberries.