Remove cinnamon rolls from the freezer and let them sit at room temperature for about 30 minutes, or until thawed just enough to cut in quarters with scissors.
While rolls are thawing, grease a 5" x 9.5" bread pan (or a pan like the one shown in the recommended products section below).
Mix 1/2 cup brown sugar and 1 tsp. of cinnamon together. Set aside.
You won't need the whole can of apple pie filling for this recipe. Spoon a cup of apples out of the saucy part of the pie filling. Roughly chop them into pieces about the size of a pea. Set aside.
As soon as cinnamon rolls are thawed enough cut them into quarters with scissors. Put rolls in a large mixing bowl.
Sprinkle brown sugar mixture over cut rolls. Toss until rolls are coated. Don't worry if all of the sugar mixture isn't stuck to the rolls.
Melt butter. Pour it over rolls. Toss to coat.
Toss chopped apple pie filling with rolls.
Pour cinnamon rolls into prepared loaf pan and cover with plastic wrap.
Let rise at room temperature until doubled in size. Or refrigerate overnight.
While rolls are rising mix flour, cinnamon, and brown sugar for streusel topping together. Cut in cold butter. Sprinkle over bread just before baking.
12. Preheat oven to 350 degrees. Bake for 35-40 minutes. I'd set the loaf pan on a baking sheet because some of that gooey apple pie filling and butter might bubble over the top and make a mess in the oven! All that messy is delicious!
Remove from the oven. Let cool for about 10 minutes. Then remove to a serving tray if desired or serve straight from the pan if you'd rather. Either way drizzle bread with icing packets that come with the cinnamon rolls.