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Preheat oven to 355 F. Grease an 11x7 in baking pan.
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If using granulated sugar, place all 5 oz of sugar into a food processor. Process on high for about 30 seconds. Measure out sugar for the base and caramel into two bowls.
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Sift flour and sugar into a medium bowl. Add butter and beat into a firm dough. Some light kneading might be necessary.
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Press dough into the prepared baking pan using the back of a spoon. Once in the pan, prick dough with a fork.
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Bake for 15-20 minutes or until pale brown in color.
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While shortbread is baking, make the caramel. Place butter, sugar, syrup, and condensed milk into a small saucepan and heat over medium low until melted. Bring mixture to a boil and let bubble for about 10 minutes, stirring constantly, until it becomes caramel colored.
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Once shortbread is baked, cool 5 minutes in the pan and then pour caramel on top of it.
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Place chocolate pieces into a double boiler and melt until smooth, stirring frequently.
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Pour melted chocolate over the caramel in a thin layer. Use a spatula to smooth if necessary. Before it hardens, gently drag a fork through the chocolate to make a swirl pattern. Leave the chocolate to set.
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Remove shortbread from pan and place onto a cutting board. Using a round cutter, about 1 ¼ inch in diameter, cut shortbread into small rounds.