Long ago, in my college years, I loved drinking gin (and got the nickname Ginni). Now, I’m loving whiskey. Whiskey sours, whiskey Cokes and most recently I’ve been diggin’ it with some root beer. You know the saying “don’t cook with alcohol you won’t drink?” Well, I prefer Kessler in my drinks (flame away, people), but I used Bulleit in these cinnamon rolls.

I used my cinnamon roll dough (but used dairy ingredients compared to non-dairy) as the starting point and made three batches of caramel before I finally got it right.

These bourbon-glazed cinnamon rolls are a decadent morning pick-me-up. Some people like coffee in the morning. Some people like tea. Everybody likes boozy cinnamon rolls. So, go into your kitchen, whip up a batch of these bad boys, and present them to someone who has a case of the morning grumpies.

Caramel Apple Cinnamon Rolls with Bourbon Glaze
makes 12 cinnamon rolls

for the dough:

3/4 cup 1% milk
1/4 cup unsalted butter
1 teaspoon vanilla extract
2 1/4 teaspoon active dry yeast
1/4 cup warm water (110°F)
3 1/2 cups all-purpose flour, divided
1/4 cup granulated sugar
1/2 teaspoon salt
1 large egg

for the filling:

4 cups diced crisp, tart apples (3 – 4 apples) – I used a combination of gala and granny smith
1 cup granulated sugar
1 1/4 cup 1% milk, warmed
1/4 teaspoon salt
1/2 teaspoon vanilla extract
2 tablespoons butter, melted
3/4 cup brown sugar
1 tablespoon ground cinnamon

for the glaze:

1 cup powdered sugar
1 tablespoon bourbon (I used Bulleit)
2 teaspoons 1% milk
1/2 teaspoon vanilla extract

to make the dough:

1. Heat milk in a small saucepan over low heat. Add in butter and vanilla and stir until melted. Remove from heat and allow to cool.
2. Meanwhile, combine yeast with warm water in a small bowl. Let sit for 10 minutes or until mixture is foamy.
3. In the bowl of a stand mixer fitted with a dough hook or in a large mixing bowl, combine 2 1/4 cups of the flour, sugar, and salt.
4. Whisk egg into the milk mixture until well combined. Pour milk and yeast mixture into the dry ingredients and mix until dough forms a sticky ball. Add in remaining flour 1/4 cup at a time, kneading well after each addition, until dough turns smooth and soft but still slightly sticky. The amount of flour you use will vary, but I usually use about 3 1/4 cups.
5. Lightly oil a large bowl. Form dough into a ball and place in bowl, turning to coat in oil. Cover and let rise in a warm place for 45 minutes.

to make the filling:

1. Place apples in a pan over medium heat and cook until softened, about 3 – 5 minutes. Remove from heat and set aside.
2. Next, prepare the caramel. Place granulated sugar in an even layer in a large pot over medium heat. Let cook, undisturbed, until sugar just starts to melt. Then, start stirring occasionally until sugar turns golden brown. Remove pot from heat and slowly (and carefully!) stir in warmed milk. Stir until well combined. If sugar hardens, don’t fret! Return the pot to the burner and cook slowly over medium-low heat. Stir constantly until the hardened sugar melts. This could take 15 minutes or longer. Continue to cook until caramel reaches desired consistency. Stir in salt and remove from heat to let cool.
3. Stir 1/3 cup of the caramel sauce in with the cooked apples and set aside. Reserve the remainder of the caramel to drizzle over the cooked cinnamon rolls.
4. Combine brown sugar with the cinnamon and set aside.

to assemble the cinnamon rolls:

1. Lightly flour your work surface. Turn dough out onto floured surface and cover with plastic wrap. Let rest for 10 minutes.
2. Roll dough out into a 20×13-inch rectangle. Spread butter onto the surface. Sprinkle with brown sugar and spread apple mixture evenly onto the surface, making sure to get it all the way to the edges.
3. Starting at the long end closest to you, tightly roll the cinnamon roll up. Gently pinch the end to seal and turn the roll seam-side down. Cut into 12 even pieces. Place rolls cut-side down into a lightly greased 9×12-inch baking pan. Cover with plastic wrap and let sit for 45 minutes.
4. Preheat oven to 350F.. Remove plastic wrap from the cinnamon rolls and bake in preheated oven for 25 – 30 minutes, or until golden brown. Allow the cinnamon rolls to cool slightly before icing so they have a chance to soak up the caramel and cinnamon sugar.
5. While the rolls are cooling, prepare the glaze. In a medium bowl, combine powdered sugar, bourbon, milk, and vanilla and whisk until smooth.
6. Drizzle glaze and caramel over the cinnamon rolls and serve.