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For the Cupcakes:
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Preheat oven to 325F.
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Combine the milk, 1 teaspoon vanilla, sugar, oil, and orange juice in a large mixing bowl.
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In another bowl, sift the baking powder, salt, baking soda, and flour together. Add the dry mixture to the wet ingredients a little at a time, mixing until smooth. Once evenly mixed, fold in the 1/4 cup orange zest. Spray 12 cupcake liners with no-stick oil spray. Fill cupcake liners and bake in the preheated oven for 22 minutes. Then remove them from the oven and allow to cool before filling and frosting.
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For the Filling:
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While the cupcakes are baking, beat the heavy whipping cream, 1 teaspoon vanilla, and 2 teaspoons confectioner's sugar in a mixer for about 5 minutes, until the cream turns light and fluffy, like whipped topping. Refrigerate the filling until needed.
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For the Frosting:
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Begin beating butter, orange flavoring, 1/4 teaspoon vanilla extract, and 1/4 cup orange zest until it starts to become fluffy. Slowly begin adding confectioner's sugar in small batches. Beat until creamy and smooth.
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Once cupcakes have cooled, use an apple corer or large frosting tip to remove the center of the cupcakes. Fill a plastic bag with the vanilla filling and cut the tip off the bag. Squeeze filling into the center of each cupcake. Then frost cupcakes with the orange frosting.
