Dry the bread (optional but recommended): Slice 8 slices of challah bread, sliced about 1 to 1.5 inches thick. For best results, place slices on a wire cooling rack on top of a sheet tray and let them sit uncovered at room temperature overnight. *If you're short on time, fresh bread still works - just watch your soak time in Step 5.
Make the custard: In a shallow bowl or baking dish (like a 9x9 Pyrex), whisk together half and half, beaten eggs, vanilla extract, ½ teaspoon cinnamon, 1 tablespoon white sugar, 1 tablespoon brown sugar, and optional orange zest. Let the custard rest for a few minutes so the sugars begin to dissolve. *Stir before each dip - cinnamon floats to the top and needs to be redistributed.
Mix the cinnamon sugar topping: In a small bowl, combine 1 tablespoon white sugar, 1 tablespoon brown sugar, and 1 teaspoon cinnamon. Stir to combine and set aside. This gets sprinkled onto the French toast right before the flip.
Preheat the griddle: Preheat your griddle to medium-low. You want slow, even heat - not a ripping hot surface. Aim for a griddle temp of about 350-375℉. When you add 2 tablespoons butter to the griddle, it should melt slowly and evenly, not sizzle aggressively.
Soak the bread: Dip each slice of challah into the custard for about 90 seconds, flipping halfway through.
Cook the first side: Place soaked slices onto the buttered griddle. Cook on the first side for about 4-6 minutes until you get a deep golden brown.
Add cinnamon sugar and flip: When the first side is deep golden brown, sprinkle a generous pinch of the cinnamon sugar topping over the top of each slice. Flip immediately. The sugar hits the buttered griddle surface and begins to caramelize, giving you a crispy crust. Cook on the second side another 4-6 minutes, or until golden and the sugar has set.
Rest and hold: Transfer finished slices to a cooling rack set inside a sheet tray. The rack keeps airflow underneath so the bottom doesn't steam and go soggy. *To hold a large batch, place the whole setup in a 200°F oven while you finish cooking the rest.
Serve: Serve with maple syrup, fresh berries, powdered sugar, or your favorite French toast toppings.