Combine milk and pudding mix in a medium bowl, stirring well with a whisk. Stir in bread until coated.
Pour bread mixture into an 8-inch square pan coated with cooking spray; sprinkle with chopped candy.
Bake at 350 for 38 minutes. Spoon pudding evenly into each of 6 individual serving bowls; top each serving with ice cream, if desired, and drizzle evenly with syrup.
Shortcut kitchen tip
To quickly chop the chocolate-covered caramel candies, place the candies close to each other on a cutting board. Then use a sharp, heavy chef's knife, and rock the knife back and forth, pressing the thickest part of the blade down on the candies.