Start by proofing your yeast. Place the warm water in the bowl of a stand mixer, add the yeast and 1 Tbsp of sugar. Let sit for about 5 minutes until it becomes foamy.
Add the 4 eggs, oil, salt and remaining sugar. Gradually add the flour one cup at a time, mixing (with the dough hook attachment on your stand mixer) to incorporate in between each addition.
If your mixer can not hold the full 8-8.5 cups of flour, transfer to a clean surface and knead the remaining flour into the dough. (I used a full 8.5 cups).
Lightly oil a large bowl and place the dough in the center of it. Cover with plastic wrap and leave in a warm, draft-free place for an hour to rise.
After an hour, the dough should be about doubled in size. Take your fist and push it down through the middle of the dough. Recover and let rise again for another 30 minutes.
Preheat oven to 375 degrees. Line 2 baking sheets with parchment paper. Divide the dough in half.
Make the cinnamon-sugar mixture. Combine all of the ingredients in a small bowl and stir to combine.
Divide each half into 4 equal balls. Roll the first ball into a log that’s about 12-18” long. Slightly flatten the long and brush the cinnamon-sugar mix onto it. Pinch it closed (back into a rolled log) and repeat this step with the other 3 dough balls.
Line the 4 strands up next to one another. Pinch the top together and fold it under so that it bakes neatly. Refer to the braiding diagram above and fold the dough into a 4 strand challah braid.
When you get to the bottom, pinch the bottom together and fold the dough under again. Place the braided challah onto one of the baking sheets. Brush the top and sides with the cinnamon-sugar and then brush the entire challah with the egg wash.
Repeat all of the steps above with the second loaf of challah bread.
Bake in the oven for 30-35 minutes (internal temperature should reach 190 degrees). Let cool before slicing. Wrap with plastic wrap or keep in an airtight container to store.
