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In the bowl of a stand mixer fitted with the dough hook, combine the milk, yeast, and brown sugar. Let sit 5-10 minutes until bubbly on top. Add the butter, eggs, flour, and salt. Using the dough hook, mix until the flour is completely incorporated, about 4-5 minutes. If the dough is still sticky, add an additional ¼ cup flour, adding more as needed until the dough is smooth to the touch.
Cover the bowl with plastic wrap and let sit at room temperature for 1 hour or until doubled in size.
Meanwhile, mix the filling. In a bowl, combine the brown sugar and cinnamon. Butter a 9×13 inch baking dish.
Punch the dough down and roll out onto a lightly floured surface, creating a large rectangle about 12 x 18 inches. Spread the jam evenly over the dough. Sprinkle on the cinnamon sugar. Starting with the long edge closest to you, roll the dough into a log, keeping it tight as you go. When you reach the edge, pinch along the edges to seal. Using a sharp knife, cut into 12-15 rolls. Place the rolls into the prepared baking dish. Cover while the oven preheats.
Preheat the oven to 350° F. Bake the rolls for 25 to 30 minutes or until golden brown.
Meanwhile, make the icing. In a bowl, whisk in the powdered sugar, maple syrup, vanilla, and a pinch of salt. If needed, thin with water or milk. Spread the icing over the warm rolls. Serve and enjoy!