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Rich brownie-like cookies filled with velvety fudge and drizzled with caramel.
Combine sugar, oil, and melted chocolate in a large mixing bowl. Beat at medium-low speed with an electric mixer until blended. Add eggs and vanilla, mixing well on low speed.
Combine flour, baking powder and salt in a medium bowl. Add about 1/3 of the dry mixture at a time into the chocolate mixture, mixing on medium-low speed after each addition. Cover the bowl with a piece of plastic wrap, put the bowl into the refrigerator and let it chill at least 2 hours.
Preheat oven to 350 F. Line 2 baking sheets with parchment paper.
Shape dough into tablespoon-sized balls. Place cookies 2 inches apart on baking sheets. Bake for 10 to 12 minutes or until set. Immediately after removing from the oven, use a flat circle-shaped surface (I used the bottom of a pizza cutter; you could also use a small shot glass or the end of a thick spoon handle) to press a crater into the center of each cookie. If you don’t have anything that works for making the imprint, just use your fingers. Cool cookies on wire racks set over a sheet of parchment paper.
Once cooled, fill the craters with fudge/chocolate sauce/ganache and set the cookies on a tray or plate. You might want to microwave the fudge for less than 10 seconds just to get it fluid. Let the filled cookies set in the freezer for a few minutes then drizzle with caramel. You can do this with a fork or use a plastic condiment dispenser.
Store in an airtight container for up to 5 days. Keep in fridge if it’s warm out.
Cookie base adapted from food.com.
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