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Chocolate Filled Chocolate Olive Oil Cookies

Yields12 ServingsPrep Time25 minsCook Time40 minsTotal Time1 hr 5 mins

How can you make chocolate cookies better? That’s easy: fill them with more chocolate. These decadent chocolate cookies start out with a rich cookie dough made with Colavita Extra Virgin olive oil, but then they get even better when wrapped around chunks of Perugina dark chocolate and then baked to toasty perfection. Fresh from the oven, the cookies ooze chocolate when bitten into, making for a particularly scrumptious surprise. A chocolate drizzle on top only completes the chocolate effect, making for a crave-worthy chocolate treat that will satisfy even the most dedicated chocoholics.

Chocolate Filled Chocolate Olive Oil Cookies

 1 ¼ cups all-purpose flour
 ¼ cup dark cocoa powder
 ¼ cup cornstarch
 ¼ tsp salt
 ¾ cup Colavita Extra Virgin Olive Oil
 ½ cup sugar
 1 egg
 1 tsp vanilla
 7 oz Perugina Bittersweet Chocolate 70%
 Optional: garnish for the top. We suggest nonpareil sprinkles, pearl sugar, grated orange peel, chopped nuts, or a dusting of confectioners’ sugar.

Unwrap your chocolate bar, and separate the bar into the 10 pre-scored squares. Set four of the squares to the side, to be used later on in the recipe.


With the remaining six squares of chocolate, cut each square into fourths. They don’t have to be perfect, but get them as even as you can. Set these 24 small squares to the side until step 8 in the recipe.


Preheat the oven to 325 degrees F. Line a baking sheet with parchment paper or a silicone mat.


In a large bowl, sift together the flour, cocoa powder, cornstarch, and salt. Set to the side.


In the bowl of a stand mixer, combine the olive oil, sugar, egg, and vanilla. Let mix for a minute or so on low speed to combine.


Pause mixing for the moment. Add the dry mix to the wet, and resume mixing on low until the mixture comes together into a pliable dough.


Divide the dough into 1 ½ inch balls. Lightly flatten each ball with your hand.


Grab those 24 small squares of chocolate you portioned out in step 2 of the recipe. In the center of each flattened portion of dough, place two of the squares, one on top of the other. Using your hands, mold each portion of dough into a ball around the chocolate, making sure there are no cracks or holes, and that the dough completely covers the chocolate on all sides.


Space the chocolate-filled balls of dough on your prepared baking sheet, spacing them evenly in three rows of four each.


Bake in the preheated oven for 14 to 18 minutes. It can be hard to detect doneness based on browning as the cookies are dark, so look for a matte appearance on the top of the dough. A gentle touch of the dough with your finger should not leave an imprint.


Remove the cookies from the oven, and let cool on the sheet for about five minutes before transferring to a wire rack to cool completely.


When the cookies have cooled, coarsely chop the four chocolate squares you set to the side in step 1 of the recipe. Melt the chocolate, and use this to drizzle the tops of the finished cookies. Garnish as desired.


These cookies will keep, stored in an airtight container in a single layer at room temperature, for up to 4 days.

Nutrition Facts

Servings 12