Heat oven to 375°F. Line cookie sheet with cooking parchment paper. Use vegetable peeler to remove rind from Brie. Cut Brie into 24 pieces. Set aside.
Unroll dough onto work surface; cut into 24 rectangles (12 rectangles from each can). Gently pull short ends of each rectangle to create square. Arrange squares on cookie sheet.
Top each square with 1/2 teaspoon raspberry preserves. Top each with 1 piece of Brie and 1 raspberry. Season with pepper. For each square, bring opposite corners of dough together over filling. Pinch to seal. Repeat with remaining dough, pinching seams to seal.
Bake 12 to 14 minutes or until golden brown. Let rest 5 minutes before serving. Serve warm or at room temperature.