Make the Cherry Filling: In a small bowl, stir together the cornstarch and water until smooth. In a small saucepan, combine the chopped cherries, sugar, and cornstarch mixture.
Bring to a simmer over medium heat, stirring often, until the mixture thickens. Remove from the heat and stir in the almond extract. Set aside to cool until needed.
Make the Dough: In the bowl of a stand mixer fitted with the dough hook, combine the yeast, warm milk, vanilla extract, and sugar. Let it sit for 2-5 minutes until the yeast dissolves and starts to activate. Add in 2 cups of the bread flour and mix to combine. Next, add the salt and egg, mixing well to form a shaggy dough.
Gradually add the remaining flour, one cup at a time, mixing until the dough begins to pull away from the sides of the bowl. Slowly add in the softened butter, one piece at a time, mixing well after each addition. Continue kneading the dough for 8-10 minutes, or until it becomes smooth, elastic, and passes the windowpane test.
Cover the bowl with a clean kitchen towel or plastic wrap and let the dough rise in a warm spot until doubled in size.
Make the Cinnamon Sugar Butter: While the dough is proofing, stir together the softened butter, brown sugar, and cinnamon in a small bowl until fully combined. Set aside.
Once the dough has doubled, line a 9x13 baking dish with parchment paper and preheat the oven to 350°F. On a lightly floured surface, roll the dough into a 10×15-inch rectangle. Evenly spread the cinnamon sugar butter over the surface. Dollop the cooled cherry filling over the top and gently spread it out.
Starting with the long edge, tightly roll the dough into a log. Slice into 12 equal pieces and arrange them in the prepared baking dish. If any of the cherry filling seeps out while rolling, simply spoon it back on top of the rolls once they’re in the pan.
Cover the dish and let the rolls proof for about 30 minutes, or until puffy.
Bake in the preheated oven for 30-35 minutes, or until golden brown and baked through. Let the rolls cool for about 5 minutes before icing.
Make the Icing & Finish: In a small bowl, whisk together the powdered sugar, heavy cream, and vanilla extract until smooth. Spread the icing over the warm rolls and serve. Enjoy!