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!

It’s October, and I’ve got a fun lineup of unique Halloween-themed recipes coming your way!
Today I’m sharing a spooky Halloween cookie idea — a fun twist on classic chocolate thumbprints! Instead of a single large center indent like traditional raspberry thumbprint cookies, these have two resembling eerie little eyes on a skull face.
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Reasons to Love These Halloween Cookies
- Make-ahead friendly – Bake the cookies in advance and freeze them! Just wait to fill with jam until after baking.
- Customizable filling – Use your favorite jam, jelly, or preserves. Red-colored ones work best for a spooky, eye-like effect.
- Perfect for school Halloween parties – They’re nut-free, making them a safe and festive treat for kids classroom celebrations.
- Delicious texture & flavor – These diy chocolate thumbprint cookies are rich, crisp on the outside, and perfectly tender on the inside.
How to make?
You can find full printable recipe below, but here is a quick overview of the procedure along with step-by-step photos.
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Success Tips
- Roll dough balls smoothly between your palms until perfectly round with no cracks or seams. This helps prevent thumbprints from splitting. If the dough cracks while rolling, apply a little pressure — the warmth of your hands will soften and smooth it out.
- Make the "eyes" using a ¼ teaspoon measuring spoon — it's the perfect size! Alternatively, the tip of your pinky finger works too.
- Fix cracks after indenting: 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!
- Use a red, seedless jam (like raspberry or strawberry) for the best “bloody eye” effect.
- Loosen the jam by microwaving it for a few seconds. This makes it easier to spoon into the indentations without mess.
- Optional spooky touch: For extra shine and a creepy glisten, add a bit more jam into the eyes after baking and just before serving at your Halloween party.
- Baking tip: Since the dough is chocolate-colored, it can be tricky to tell when they’re done. Gently press a cookie — it should feel firm to the touch when fully baked.
- 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.
Chocolate Thumbprint Cookies for Halloween
Equipment
Ingredients
- 1 cup all purpose flour
- ½ cup cocoa powder
- ⅛ teaspoon salt
- ½ cup unsalted butter (1 stick) at room temperature
- ½ cup sugar
- 1 teaspoon vanilla extract
- 1 egg yolk
- ⅓ cup strawberry jam or any red seedless jam
Instructions
- Add the flour, cocoa powder and salt into a small bowl and whisk to combine.
- Place butter, sugar and vanilla into a large bowl and beat using an electric beater until smooth and creamy, for about 2 minutes.
- Add egg yolk and beat well.
- Add the flour mixture and mix on low speed until the dough begins to come together. Then use your hands to shape it into a smooth ball.
- Scoop the cookie dough into heaping tablespoon-sized portions and roll each one smoothly between your palms until perfectly round, with no cracks or seams — this helps prevent thumbprints from splitting.
- Place the shaped discs on a parchment-lined baking sheet, spacing about 1 to 2 inches apart.
- Use the rounded back of a ¼-teaspoon measuring spoon (alternatively, the tip of your pinky finger works too), gently press an indent on one side of the cookie dough. Repeat on the other side to create two eyes. 👉 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!
- Place the baking sheet in the fridge for at least 2 hours to firm.
Bake
- Preheat oven to 350°F (175°C).
- Place the jam in a microwave-safe bowl and warm it for about 20 seconds, stirring every few seconds, until it’s loosened and easy to spoon.
- Using a small spoon, carefully fill each cavity with a bit of jam — just enough to fill without overflowing, as it will spread while baking.
- Bake cookies for 25 to 30 minutes, or until the cookie feels firm to the touch. 👩🍳 Since the dough is chocolate-colored, it can be tricky to tell when they’re done. Gently press a cookie — it should feel firm to the touch when fully baked.
- Place the pan on a wire rack, cool the cookies and store!
Optional step
- For an extra spooky touch, you can add a little more jam to the 'eyes' on the day of serving — the added jam gives them a glossy, eerie finish that's perfect for Halloween!
- To do so, microwave a bit of jam as before to loosen it, then spoon it into a small zip-top bag. Snip off the corner and gently pipe a little jam into each “eye.” Let the cookies sit for a few hours so the jam can set slightly.If you're storing or transporting them, be sure to keep the cookies in a single layer to prevent the jam from smudging.
Notes
Nutrition
Nutritional information, based on third-party calculations, should be seen as estimates, not guarantees, as various factors like product types, brands, processing methods, and more can alter the nutritional content in recipes.

More Cookie Recipes for Halloween
- Spooky Halloween tree cookies are an easy Halloween baked good to impress your kids. They are buttery, crisp, and amazingly tender!
- These Halloween skull cookies are cute, easy, and a unique Halloween cookie recipe. They’re skull-shaped Linzer cookies, filled with jam and topped off with an adorable M&M flower.
- These Halloween finger cookies with almond nails are easy to make and an eggless shortbread cookie!
- These candle cookies are made using buttery, crisp chocolate shortbreads and are shockingly easy to make. They are fun, creative and impressive, and no special tools are needed.
- These Halloween bone cookies are made without cookie cutters! It is an easy, unique cookie to make from scratch and is a fun baking project for kids to make and safe for humans.
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