In a small bowl, dissolve the yeast in warm water with 1 tablespoon of sugar. Let it sit for 5-10 minutes until it becomes foamy.
Make the Dough:
In a large mixing bowl, combine the remaining sugar, warm milk, melted butter, vanilla extract, and salt. Stir to combine.
Add the activated yeast mixture to the bowl and mix well. Gradually add the flour, one cup at a time, stirring with each addition until a dough forms.
Once the dough comes together, turn it out onto a floured surface and knead for about 8-10 minutes, until the dough is smooth and elastic. Add more flour if needed to prevent sticking.
Let the Dough Rise:
Grease a large bowl with butter or cooking spray, then place the dough in the bowl, turning it to coat all sides. Cover the bowl with a clean cloth and let the dough rise in a warm place for 1-1.5 hours, or until it has doubled in size.
Prepare the Cinnamon Filling:
While the dough is rising, prepare the cinnamon filling. In a small bowl, combine the softened butter, brown sugar, and ground cinnamon. Mix until smooth and well combined.
Shape the Bread:
Once the dough has risen, punch it down to release any air bubbles. Turn it out onto a floured surface and roll it into a large rectangle (about 12×16 inches).
Spread the cinnamon filling evenly over the dough, leaving a small border around the edges.
Starting from the long side, carefully roll the dough into a tight log, then pinch the edges to seal.
Bake the Bread:
Preheat the oven to 350°F (175°C). Grease a 9×5-inch loaf pan and place the rolled dough into the pan. Let the dough rise for another 20-30 minutes, until it puffs up slightly.
Bake for 30-35 minutes, or until the top is golden brown and the bread sounds hollow when tapped on the bottom.
Make the Icing:
While the bread is baking, prepare the icing. In a small bowl, whisk together the powdered sugar, melted butter, vanilla extract, and milk until smooth and drizzle-able. Adjust the milk as needed to achieve the desired consistency.
Glaze the Bread:
Once the bread is done baking, remove it from the oven and let it cool for about 10 minutes before transferring it to a cooling rack.
Drizzle the icing generously over the warm bread, allowing it to soak in slightly.
Serve and Enjoy:
Slice the bread into thick, fluffy slices and serve warm. It’s perfect for breakfast, brunch, or as a sweet treat any time of day.
Serving and Storage Tips:
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