Preheat oven to 350 degrees. Prepare foil pan with nonstick spray. Prepare a baking sheet with foil. Cut brioche into 1" dice (does not need to be perfect), place on baking sheet, and bake approximately 15 minutes, or until they are golden brown. Remove from oven, place in a medium mixing bowl, and set aside.

In a small pot, combine milk, half of the sugar, cinnamon, butter, and a pinch of salt. Heat to a simmer on medium-high heat. While milk mixture is heating up, in a medium mixing bowl, combine eggs, yolk, remaining sugar, and vanilla extract and whisk to combine. Once milk mixture starts to simmer, reduce heat to low and add chocolate. Stir until chocolate is melted and remove from heat.

Slowly whisk (temper) hot milk/chocolate mixture it into egg mixture. (To keep your bowl from spinning while whisking, put a towel underneath to stabilize it.) Once combined, cover the bowl with plastic and let it sit at room temperature for 20 minutes. The plastic will steam up and dome slightly: this is normal.

After 20 minutes, uncover egg/milk mixture and reserve 3/4 cup. Pour remaining mix over the toasted brioche pieces in a bowl. Add dried cherries and gently stir to coat using your hands, a large spoon, or rubber spatula. Let sit for 5 minutes to soak up the liquid.

Fill foil pan with soaked bread. Pour any remaining soaking liquid over the bread, enough to see it at the edges of the foil pan.

Bake for approximately 23-25 minutes. The top with be slightly set but will still have a give and the sauce will be bubbling a little around the edges. Let cool for 5 minutes and serve with remaining sauce! (The sauce is the remaining soaking liquid, which is excellent with the pudding!)