Prepare a 9×13 inch baking dish with butter or cooking spray (bottom and sides) and set aside.
Whisk together the sugar and the yeast.
Heat the milk until warm (not hot), and pour into a bowl (either a mixing bowl and use a hand mixer, or the bowl of a stand mixer). Add in the whisked sugar and yeast mixture and whisk by hand, the sugar and yeast into the milk. Cover with a towel and let sit until the yeast is foamy, about 5-10 minutes. The yeast should dissolve and foam.
Next, on low speed, beat in the softened butter (8 TBSP),, and next the eggs, one at a time, and then add the salt. Gradually add the flour and beat on medium speed until the dough is soft, about 5 minutes. Or, knead by hand.
On a lightly floured board or surface, lay down the dough and knead it with your hands for 1 minute.
With your hands, make a ball with the dough and transfer to a bowl that has been lightly greased. Cover with plastic wrap or a towel and set it in a warm place for 1-2 hours, until the dough has doubled in size.
Next, place the risen dough onto a lightly floured work surface, punch it down and roll into a 16×24 inch even rectangle.
Make the apple pie filling:
While the dough is rising, make the apple pie filling. Heat 4 tablespoons of the butter and the ½ cup granulated sugar in a large skillet over medium heat, then add the chopped apples and raisins. Sauté apple mixture on medium-high heat until slightly caramelized (about 4-5 minutes). Remove from heat and set aside.
In a separate small bowl, mix the dark brown sugar, cinnamon and cardamom and set aside.
Assemble the cinnamon rolls:
On top of the rolled out dough, spread the remaining 2 Tbsp of softened butter almost out to the edges.
Sprinkle the dark brown sugar mixture evenly over the butter. Next spread the apple mixture over the brown sugar as evenly as you can.
Roll into a log, starting from one end to the other, lengthwise, so the log is 24 inches.
Using a sharp knife, gently cut 2 inch slices with a sawing motion (don’t squish or pinch the dough to flatten), to create 12 cinnamon rolls.
Place each roll in the prepared 9x13 baking pan. Cover the baking dish very tightly with plastic wrap or aluminum foil. Allow rolls to rise in a warm place again for about 45-60 minutes to rise, or until the rolls are doubled in size.
Bake the rolls:
Preheat the oven to 375°F. Bake rolls for about 22-25 minutes until they are golden brown. The last 15 minutes, cover the rolls loosely with foil to prevent the tops from browning too much. Remove from the oven and allow to cool on a wire rack for 5 minutes.
Make the icing:
In a small bowl, whisk the frosting ingredients and drizzle over the warm rolls. Serve warm.
Cover leftover frosted or unfrosted rolls tightly and store for up to 3 days at room temperature or up to 5 days in the refrigerator.
Notes
Make Ahead InstructionsOvernight: To prepare the night before serving, prepare the rolls through step 4. Cover the rolls tightly and refrigerate for 8-12 hours. The next morning, remove from the refrigerator and allow to rise on the counter for 1-2 hours before continuing with step 6.Freezing: Baked rolls can be frozen for up to 2-3 months. Thaw overnight in the refrigerator and warm up before enjoying.