These Chocolate Thumbprint Cookies are made with a simple sugar cookie dough, indented to resemble skulls and filled with red strawberry jam! It is a unique, fun, creative, spooky cookie idea for Halloween!
Mix dry ingredients. Add 1 cup flour, ½ cup cocoa powder and ⅛ teaspoon salt into a small bowl and whisk to combine.
Cream butter and sugar. Place ½ cup butter, ½ cup sugar and 1 teaspoon vanilla into a large bowl and beat using an electric beater until smooth and creamy, for about 2 minutes. Add 1 egg yolkand 1 tablespoon milk; beat well.
Finish dough. Add the flour mixture and mix on low speed until the dough starts to come together.👉 To test the consistency, roll a slightly heaped tablespoon of dough into a ball and press your pinky finger into it twice to make the eyes. If the dough develops large cracks, mix in ½ tablespoon of milk and test again. Repeat with another ½ tablespoon of milk if needed. The dough should be soft enough to shape without cracking too much, but still firm enough to hold its shape. Adding too much milk can cause the cookies to spread during baking.Once the dough reaches the right consistency, roll it into a smooth ball by hand.
Make balls. Scoop the dough into slightly heaping tablespoon-sized portions and roll each one between your palms until smooth and round and then flatten them a uniform thick disc. Place the disks on a parchment-lined baking sheet, spacing them about 1 to 2 inches apart.
Make eyes. Using your pinky or index finger, make two deep indents in the dough to resemble eyes, pressing about ¾ of the way down. You can also use a ¼-teaspoon measuring spoon, but I find your finger creates a deeper indent that holds more jam.👉 If the dough cracks around the edges after making the "eye" indentations, simply pinch and smooth it back together. But don’t stress — a few imperfections actually add to the spooky look!
Chill. Place the baking sheet in the fridge for about 30 minutes.
Prep. Preheat the oven to 350°F (175°C) before baking.
Fill cookies. Place the ⅓ cup jam in a microwave-safe bowl and warm it for about 20 seconds, stirring every few seconds, until loosened. Transfer the jam to a small piping bag or zip-top bag, snip off the corner, and squeeze a little into each cavity, filling to the brim.
Bake. Bake for 25 to 30 minutes, until the cookies feel firm to the touch. Since the dough is chocolate-colored, it can be hard to tell when they’re done by appearance alone, so gently press the center of a cookie—it should feel firm when fully baked. Place the baking sheet on a wire rack and let the cookies cool completely before storing.
Optional step. For an extra-spooky touch, squeeze a little more jam to the “eyes” on the day you serve the cookies. The fresh jam gives them a glossy, eerie finish that’s perfect for Halloween. Let the cookies sit for a few hours afterward so the jam can set slightly.👉 If you’re storing or transporting them, keep the cookies in a single layer to prevent the jam from smudging.
Video
Notes
Use a red, seedless jam (like raspberry or strawberry) for the best “bloody eye” effect.Storage: Store cookies in an airtight container for up to 3 days. For the best texture, fill the jam just a few hours before serving.