Warm milk to 90-100 degree F. Melt butter to 90-100 degree F. Crack and beat up a room temperature egg. Combine milk, butter and egg into a bowl or a standing mixer.
Add dry ingredients to mixture: flour, sugar, salt, yeast and raisins. Use a dough hook to mix the dough if using a standing mixer. Or knead the dough with hand.
Dough should not be sticky, but it shouldn't be very dry either. When touch with fingers, a large clump of dough should not stick to fingers. Start with 3 3/4 cup flour and add more if dough is sticky. A lot of factors (humidity, temperature, size of egg etc) can make the dough more or less wet, so the amount of flour needed may differ slightly.
Lightly butter large bowl (bowl must be twice or three times larger than dough) and bring dough to bowl. Cover with cloth, and let it rise for an hour, preferably in a warm spot.
Dough should rise to twice its original size.
When dough has risen, punch the ball with your fist to release the air. Flour a clean surface, then use a rolling pin to flatten out dough into a 15″x12″ rectangle.
To make apple pie filling
Melt butter in a medium pot under medium heat. Once butter is melted, add apples, brown sugar, cinnamon, vanilla extract, flour and a pinch of salt. Bring heat to medium high and stir continuously. Use a whisk to whisk and remove clumps from the mixture if needed.
Once mixture comes to a boil and has thickened, remove from heat promptly by transferring to a separate bowl (so that mixture does not continue cooking) and set aside.
Cool mixture so that it is not boiling hot (slightly warm or room temperature is fine) when added to the dough. (See Note 1)
To make Apple Pie Cinnamon Rolls
Spread apple pie filling evenly onto the flattened dough. Leave a 1-inch frame around the dough where there is no apple pie filling. Doing this will prevent less filling from spilling out of the dough when rolling the dough.
Gently roll dough from the long side into a long tube.
Using a serrated knife, cut off the ends and then cut tube into 12 cinnamon rolls. Each roll will be about an inch thick.
Place rolls onto a 9″x13″ casserole dish lined with parchment paper, or greased with butter. Rolls may be soft and apple pie filling may ooze out while transferring the rolls. A little messy is ok and expected! :)
Cover casserole dish with a towel and let rolls rise again for 30 minutes.
Preheat oven to 350 degrees F.
Remove towel. Cinnamon raisin rolls should be slightly bigger in size. Bake in oven for 22-25 minutes.
While rolls are baking, make the glaze by combining all the ingredients under “Icing/glaze” using a hand mixture or a whisk. Add more powdered sugar to make thicken the glaze and add more milk to thin out the glaze based on your preference.
When rolls are done, let it cool for 10 minutes. Drizzle glaze onto the rolls.
Serve and enjoy!
Note 1: To ensure that apple pie filling has time to cool, make filling immediately after placing the dough to rise. This way there is time for the filling to cool while the dough rises.