Combine 2 1/2 cups of sugar, water, vanilla, and orange extract in a sauce pan. Heat over medium until the sugar has completely dissolved, but not boiling.
Pour in the cranberries and stir. The hot syrup will loosen the skin, saturate the berries, and adhere to the berries over time. Cover the cranberries with a small plate to keep them mostly submerged. Then cover the pan and place it in the refrigerator over night.
Place the remaining 1 1/4 cup of sugar in a rimmed dish. Strain the cranberries and place them in the sugar. Shake until they are completely coated. Carefully transfer them to a baking sheet to dry, about an hour.
Once the sugar coating is hard, place them in an air-tight container and keep in a cool spot for up to a week.
NOTE: Don’t forget to refrigerate your Cranberry Infused Vanilla-Orange Syrup for cocktail time!