1. Proof Yeast: In a small bowl or measuring cup, combine the warm milk, yeast, and 1 tablespoon of the granulated sugar. Stir gently and let sit for 5–10 minutes until the mixture is foamy.

2. Mix Wet Ingredients: In a large bowl or stand mixer, whisk together the melted butter, egg, apple cider vinegar, and the yeast mixture.

3. Mix Dry Ingredients: In a separate medium bowl, whisk together the gluten free flour, baking powder, salt, and the remaining granulated sugar.

4. Make Dough: Add the dry ingredients to the wet ingredients. Mix on low speed (or by hand) until a soft, sticky dough forms. The dough will be stickier than traditional wheat dough—do not add extra flour.

5. Prepare Coating: In a small bowl, mix the brown sugar and cinnamon together. Place the 1/2 cup melted butter in a separate shallow bowl. Grease a standard bundt pan heavily with butter or non-stick spray.

6. Shape & Coat: Scoop about 1 tablespoon of dough at a time. Roll it gently into a ball between your palms (greasing your hands helps). Dip the ball into the melted butter, then roll it in the cinnamon-sugar mixture until coated. Place into the prepared bundt pan.

7. Repeat: Continue rolling and coating until all dough is used, stacking the balls unevenly in the pan.

8. Rise: Cover the pan with plastic wrap and place in a warm, draft-free spot. Let the dough rise for 45–60 minutes. The dough won’t double in size, but it should look puffy.

9. Bake: Preheat oven to 350°F (175°C). Remove plastic wrap and bake for 30–35 minutes, or until the top is golden brown and the center is set.

10. Cool & Flip: Let the bread cool in the pan for exactly 10 minutes. Then, carefully invert the pan onto a serving plate. (If you wait too long, the caramel will harden and stick).

11. Glaze: Whisk together the powdered sugar, milk, and vanilla until smooth. Drizzle over the warm bread and serve immediately.