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Preheat oven to 425°F. Spray Wilton non-stick ice cream cookie bowl pan with cooking spray. (Alternatively, line a muffin tin with 10 liners.)
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Melt chocolate and butter in large microwaveable bowl on high, until butter is melted. (Approximately 1 minute.) Stir with whisk until chocolate is completely melted.
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Stir in powdered sugar.
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Add whole eggs and egg yolks and vanilla and mix well.
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Stir in flour and cinnamon until blended.
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Fill cups halfway full of batter and add caramel candy, pressing down slightly. Top with remaining batter, filling approximately 2/3 full.
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Bake for approximately 10 minutes or until sides of desserts are firm but centers are still soft. Let stand 1 minute.
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Carefully loosen edges and invert on large cutting board or platter. Transfer to dessert plates, still upside down.
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Top with a scoop of your favorite ice cream, caramel topping and a cherry if desired.