Pour 2 cups of apple cider into a small saucepan and set it over medium heat. Bring it to a gentle simmer and cook, stirring occasionally, until it reduces down to about 1¼ cups — this should take about 10 minutes. You’ll know it’s ready when it’s slightly more syrupy and fragrant. Remove from heat and let it cool until slightly warm.
In a large mixing bowl or the bowl of a stand mixer, add the 1¼ cup reduced cider, 2¼ tsp yeast and 2 tbsp brown sugar. Mix and allow to stand until it becomes foamy/ bubbly, about 5 minutes.
Add remaining bread ingredients of 4 tbsp melted butter, 1 egg, 3½ cups all purpose flour, ½ tsp salt, 2 tsp apple pie spice and remaining ¼ cup brown sugar. Stir until all ingredients are combined and a shaggy dough forms. Transfer to a clean, floured surface and bring the dough together with your hands, adding up to ½ cup more flour as needed if too sticky. Knead for about 5 minutes. (*If using a stand mixer, mix ingredients with a dough hook and knead for same time).
Place kneaded dough ball in a lightly oiled large bowl and cover with clear wrap or a towel and let rise in a warm, dry place for 1 hour, or until doubled in size.
While dough is rising, mix cinnamon filling ingredients of 6 tbsp softened butter, ¾ cup brown sugar and 1 tbsp cinnamon together in a bowl until smooth.
Transfer risen dough to a cleaned, floured surface and roll it out into a wide, thin rectangle, about ½" thick. Spread cinnamon filling using a rubber spatula or back of spoon evenly across dough, reaching corners. Roll lengthwise as you would cinnamon rolls and fold the long log in half, pressing the seams of dough together. Using a knife or pastry cutter, cut two seams into the dough, leaving 1” connected at the top, so you are left with three dough strands to braid. Overlap pieces into a braid and pinch seam at end to seal pieces together. Transfer to a parchment lined 9×5" loaf pan, cover with a towel and let rise once more for 30 mins.
Bake at 350℉ for 45-60 minutes, covering with foil half way through to avoid browning. Internal temperature should read 190℉ in the center of the bread, baking times vary depending on oven and size your loaf rose to.
Remove from oven and allow to cool on a baking rack for at least 20 minutes before adding donut coating. Slice and enjoy!