In a large mixing bowl, whisk together your flour, salt, yeast, and sugar from the bread dough ingredients.
3 Cups Flour, 1¾ Tsp Salt, 1 Tsp Instant Yeast, 1 Tsp Sugar
Add the oil and water to the dry ingredients and mix until thoroughly combined into a dough. Cover the dough and let it sit for 15 minutes to settle.
1¼ Cup Warm Water, 1½ Tbsp Olive Oil
Grab the dough from a side of the bowl, pull it toward the center, and press down. Repeat while circling around the dough until you work all the way around, about a dozen times. This lightly kneads the dough. Flip the dough ball over so the smooth side is up. Cover and let the dough rest another 15 minutes, then repeat.
¼ Cup Cinnamon Baking Chips
After your third 15 minute rest and second fold (so before your third fold), sprinkle half of your cinnamon chips over the dough and fold them in. Do the same before your fourth fold with the other half of the cinnamon chips.
Cover the dough and let it rise in a warm room for a full hour.
Prepare your baking dish by greasing it and lining it with parchment paper to make it easier to remove the bread when it's done. Add a tablespoon of olive oil to the pan on top of the parchment paper here too.
3 Tbsp Olive Oil
Transfer your dough to the pan, gently so as not to fully knock the air out of it. Once more, cover and let rise for another hour.
Make your filling by combining the butter, sugar, and cinnamon.
⅓ Cup Brown Sugar, 2 Tbsp Butter, 1 Tbsp Cinnamon
When the rise is almost complete, preheat your oven to 450℉.
Use some of the excess oil to coat your fingers and poke dimples into the bread dough, pressing to reach the bottom of the pan (but not so deep it breaks through). You don't want to fully deflate the dough, just add pockets for the cinnamon filling throughout.
Sprinkle your filling across the bread, making sure extra fills the dimples. Drizzle any remaining oil over the top of the dough.
Bake your bread for 15-20 minutes. You're looking for the topping to be bubbly and the bread to be golden brown.
Remove the bread from the oven and the baking dish, transferring to a wire rack to cool.
Make your icing by mixing together the milk, powdered sugar, and vanilla. Drizzle or spread this over the bread (depending on the consistency you prefer, adjust with more milk or sugar) and cut to enjoy.
¾ Cup Powdered Sugar, 1½ Tbsp Milk, ½ Tsp Vanilla Extract