Preheat your oven to 350°F. In a large bowl, whisk together the whole-milk yogurt, 1 cup of sugar, eggs, orange zest, vanilla, and vegetable oil until perfectly smooth. Pro Tip: The heavy lactic acid in the whole-milk yogurt naturally relaxes the flour's gluten networks, which guarantees a tender texture that won't turn tough or bready.
In a separate small bowl, toss your dry cranberries with the 1 tablespoon of reserved flour until they are fully coated in a white powder.
Sift the remaining dry ingredients into the wet yogurt base. Using a rubber spatula, fold gently just until the flour disappears. At the last moment, fold in the floured cranberries. The flour dust binds to the thick batter, keeping the heavy, tart berries suspended evenly throughout the loaf instead of sinking into a mushy layer at the bottom.
Pour the batter into a greased and floured 9×5-inch loaf pan. Bake for 50–55 minutes. Check the center with a toothpick—it should come out with just a few moist crumbs attached. Let the loaf sit in the pan for exactly 10 minutes, then invert it onto a wire rack set over a rimmed baking sheet.
While the loaf cools slightly, simmer the 1/3 cup of orange juice and 1/3 cup of sugar in a small saucepan over medium heat until the sugar dissolves completely. Continue boiling for 3 more minutes to yield a thin, concentrated citrus glaze.
Use a toothpick to poke deep holes across the top and sides of the warm loaf. Using a pastry brush, generously paint the entire surface with the hot orange syrup. Let it soak into the crumb for 5 minutes, then repeat until all the syrup is used. This forces intense orange flavor directly into the core of the bread.
Let the loaf cool completely to room temperature. Whisk the confectioners' sugar and remaining orange juice until it forms a thick, glue-like consistency. Pour it directly over the top of the loaf, allowing it to drip casually down the sides into a opaque, crackly crown.