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1. In a large bowl, beat butter with an electric mixer on medium to high speed for 30 seconds. Add sugar, baking powder, and salt. Beat until combined, scraping bowl occasionally. Beat in egg, milk, and vanilla until combined. Beat in as much of the flour as you can with the mixer. Stir in any remaining flour with a spatula or wooden spoon. Divide dough in half. Cover and chill for 2 hours or until dough is easy to handle.
2. Preheat oven to 375 degrees F. Line cookie sheets with parchment paper or foil; set aside. On a lightly floured surface, roll half the dough to 9x8-inch square. With a pastry wheel or pizza cutter, cut into eight 4-1/2x2-inch rectangles. Place a Ghirardelli Milk & Caramel SQUARES (TM) Chocolate near one end of each rectangle. Bring the dough strip up and over the chocolate square, pinching dough to enclose the chocolate square. Place on prepared cookie sheets. Repeat with remaining dough and chocolate squares.
3. Bake for 12 minutes or until edges are firm and very lightly browned. Transfer cookies to a wire rack; cool.
4. Meanwhile, for the chocolate drizzle, in a small microwave-safe bowl, combine the Ghirardelli® 60% Cacao Bittersweet Chocolate Baking Chips and shortening. Cook on medium power (50 percent) for 1 minute. Remove and stir. If chocolate is not melted, return to microwave and repeat heating step, stirring every 30 seconds to avoid scorching. Stir until smooth.
5. Spoon the chocolate drizzle over cookies. Let cookies stand in the freezer or at room temperature until the drizzle is set.
6. Enjoy immediately, store in an airtight container at room temperature for up to 3 days, or freeze for up to 3 months.