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Add eggs, half and half, vanilla, cinnamon, salt, cocoa powder and one Instant packet or two cocoa k-cups to a large mixing bowl. Whisk well to combine until the mixture is smooth and shiny.
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Add the challah bread pieces to the bowl in a few batches. Gently stir to make sure the bread is coated and it absorbed the mixture.
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Add bread to the prepared baking dish and top with chocolate chips, repeat with the remaining bread. Pour any remaining chocolate mixture over the bread.
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Add butter and brown sugar to a small sauce pan and melt over medium heat, stirring continously for about 5-7 minutes. When the mixture is smooth and shiny, pout it over the bread. Wrap tightly with plastic wrap and place in refrigerator overnight.
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Preheat oven to 350F.
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Allow the casserole to stay at room temperature for 10-15 minutes before transferring to the oven.
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Bake for about 30-35 minutes until golden brown. Start checking at 25 minutes.
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Once it bakes, serve immediately, preferably with maple syrup and fresh fruits!