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Preheat the oven to 350 degrees Fahrenheit. Line a metal loaf pan with parchment paper or grease the pan generously with oil.
Zest one orange to make about 1 tablespoon of zest. Place the zest and the sugar into a large mixing bowl together. Stir zest into sugar, helping to release the orange flavor into the sugar.
With an electric mixer in a large bowl, cream the sugar with the butter.
Crack the egg and beat it. Add the egg and vanilla, then mix into the butter mixture until smooth. Add the milk and orange juice and mix until combined.
Add flour, baking powder, and salt into a second bowl and mix until well combined. Then add the dry ingredients to the wet ingredients and mix well until a batter forms and is fully blended.
Toss the cranberries with a teaspoon of flour.
With a silicone spatula, fold the cranberries into the batter. Pour batter carefully into the prepared loaf pan.
Bake for 65-70 minutes or until a toothpick inserted in the center comes out clean.
Cool the loaf for at least 15 minutes before removing from the pan. Cool loaf completely on a wire rack before glazing.
In a medium-sized bowl, add powdered sugar, one tablespoon orange juice, one teaspoon orange zest and milk. Whisk together until a smooth glaze forms.
Drizzle glaze over the loaf and let glaze set for at least 30 minutes.