Ingredients

2 cups Bob’s Red Mill Organic Unbleached All-purpose Flour

½ cup unsweetened Dutch-process cocoa powder

½ teaspoon salt

1 8 ounce bag milk chocolate toffee bits, divided

1 cup + 1 tablespoon butter at room temperature

1 cup sugar

1 large egg at room temperature

1 teaspoon vanilla extract

Filling:

4 ounces semi-sweet chocolate chips

1 tablespoon butter softened

⅓ cup heavy cream

½ cup sifted confectioners’ sugar

Instructions

Step 1: Whisk the flour, cocoa, and salt together in a medium bowl. Add 1 cup of the toffee bits and toss to coat evenly.

Step 2: In a separate large bowl, beat the butter and sugar together on medium speed for about 2 minutes. Scrape down the sides of the bowl.

Step 3: Beat in the egg and vanilla extract until fully combined.

Step 4: Add the flour mixture to the wet ingredients and mix with a spoon. Once the dough thickens, gently knead it to evenly disperse the toffee bits.

Step 5: Roll the dough into 1-inch balls and place them on a parchment-lined baking sheet. Use your thumb or the end of a wooden spoon to press a well into the center of each ball.

Step 6: Refrigerate the cookies for at least 30 minutes to firm up.

Step 7: Preheat the oven to 350°F (175°C). Line baking sheets with silpats or parchment paper. Place the chilled cookies about 1 inch apart on the sheets.

Step 8: Bake for 8 to 9 minutes. After baking, press the center wells again with a wooden spoon or cookie scoop if needed.

Step 9: Cool the cookies completely on the baking sheets, then transfer to wire racks. Repeat baking with remaining chilled dough.

Step 10: To prepare the filling, gently heat the semi-sweet chocolate chips, softened butter, and heavy cream until smooth. Stir in the sifted confectioners’ sugar until combined.

Step 11: Spoon or pipe the chocolate filling into each thumbprint well once cookies are fully cooled. Let set before serving.

Tips & Variations

For an extra crunch, use dark chocolate toffee bits instead of milk chocolate.

Chilling the dough is key to preventing spreading and keeping the thumbprint shape.

Try adding a pinch of espresso powder to the dough to enhance the chocolate flavor.

Substitute the filling with caramel or peanut butter for a different twist.

Storage

Store the cookies in an airtight container at room temperature for up to 5 days. For longer storage, keep them refrigerated for up to 2 weeks. If refrigerated, bring to room temperature before serving. The filled cookies can also be frozen for up to 3 months; thaw in the refrigerator overnight and allow to come to room temperature before enjoying.

FAQs

Can I use regular cocoa powder instead of Dutch-process?

Yes, you can substitute regular cocoa powder, but it may affect the final flavor slightly, giving it a more acidic and sharper chocolate taste.

How do I make sure the thumbprints don’t disappear during baking?

Chilling the dough before baking helps keep the indentations. Also, gently pressing the thumbprint wells again right after baking ensures they stay visible and ready for filling.