Make Brioche Dough

• Place flour, cinnamon, yeast, sugar and salt into the bowl of a stand mixer and whisk together evenly.
• Add the eggs and milk and mix on low speed with dough hook for 4 minutes (the dough should hold together in a loose ball).
• Gradually add the butter piece by piece, mixing well to incorporate after each piece. The dough will seem to fall apart while mixing in the butter. After all the butter has been added, continue mixing on low to medium-low speed until the dough forms a tight ball around the dough hook again. This process may take 30 minutes. The final dough should be about 75–77°F (24–25°C).
• Transfer dough to an oiled bowl or container and cover. Ferment at room temperature for 1 hour. The dough will not rise very much in this hour.
• Fold the dough by stretching from top, bottom, and either side, then flip the dough over. Cover and refrigerate for at least 4 hours and preferably overnight.

Next Day

Make Cinnamon Filling

• Place the room temperature butter into the bowl of a stand mixer fitted with the paddle attachment and mix on medium speed until the butter is fluffy and light.
• Whisk together the powdered sugar and add to the butter. Mix on low speed until incorporated. Scrape down the sides with a spatula.
• Add the egg and mix on medium speed so the mixture is fluffy. Scrape down the sides of the bowl.
• Add the almond flour, flour, and cinnamon and mix on low speed to combine. Scrape down the sides of the bowl and mix again.
• Set the filling aside while you roll the brioche dough.

Shape

• Pull the brioche dough from the refrigerator. Scrape the dough from the bottom of the container and invert onto lightly floured work surface.
• Roll out into a 12 x 15″ rectangle that is 1/4″-thick.
• Spread the cinnamon filling all over the dough with an angled spatula, leaving a 1″ border on one of the long sides uncovered.

• Lightly moisten the 1″ border of dough with water. Roll up the dough into a log starting with the long edge that has the cinnamon filling spread all the way to the border.
• Pinch the moistened edge of the dough to seal the seam. Shape the log so that its diameter is even all the way across. Position the rolled log so that it’s seam-side down.

• Using kitchen twine, cut 3/4″ slices through the length of the log.

Proof

• Place the cinnamon rolls onto a parchment-lined baking sheet. Lightly spray with cooking spray and cover with plastic wrap.
• Proof (last fermentation after shaping) the cinnamon rolls at room temperature until they have increased in volume, and an indentation springs back when you press the edge of the dough with your finger. You should see and feel that bubbles have developed in the dough.

Bake

• Preheat oven to 350°F (177°C). Once proofed, bake the cinnamon rolls for 20-30 minutes.
• When the cinnamon rolls are lightly golden brown, spot-check their internal temperature with a Thermapen to test their doneness. Their internal temperature should be 190–200°F (88–93°C).
• If the internal temperature is below 190°F (88°C), continue baking for a minute or two longer and spot-check the internal temperature again.

Finish and Serve

Once they’re done, remove them from the oven, allow them to cool somewhat, ice them, and serve!