Ingredients (Yields ~20 cookies)

For the Fennel Sugar

• 1/4 cup granulated sugar
• 1 tablespoon whole fennel seeds

For the Cookie Dough

• 3/4 cup granulated sugar
• 1/2 cup packed light brown sugar
• 1 cup (2 sticks) unsalted butter, at room temperature
• 1 vanilla bean (or 2 teaspoons vanilla extract)
• 1 large egg, at room temperature
• 2 1/4 cups all-purpose flour
• 1/2 teaspoon baking powder
• 1/4 teaspoon baking soda
• 1/2 teaspoon salt
• 3.5 oz (100 g) dark chocolate (70% or higher)

Make the Fennel Sugar

You can make this sugar up to a month in advance.

Add the 1 tablespoon of fennel seeds to a small, dry frying pan over medium heat. Toast the seeds, shaking the pan, until they are very fragrant. This only takes about one minute.

Transfer the toasted seeds to a spice grinder or a mortar and pestle and grind them until they are relatively fine.

In a small bowl, stir the ground fennel into the 1/4 cup of granulated sugar. Set this aside.

Cream the Butter and Sugars

Preheat your oven to 350°F (180°C).

In the bowl of a stand mixer with the paddle attachment, add the 3/4 cup granulated sugar, 1/2 cup brown sugar, and 1 cup of softened butter.

Beat on medium speed for ~4 minutes until the mixture is smooth, fluffy, and has lightened in color. Scrape down the sides of the bowl and the paddle halfway through.

If you don’t have a stand mixer, you can use a hand mixer and a large bowl.

If you’re using a vanilla bean, split and scrape it. Add the seeds and the 1 large egg to the butter mixture. Mix for about one more minute to combine everything.

Form the Cookie Dough

In a separate medium bowl, whisk together the 2 1/4 cups of flour, 1/2 teaspoon of baking powder, 1/4 teaspoon of baking soda, and 1/2 teaspoon of salt.

Add these dry ingredients to the butter mixture and mix on low speed.

Stop mixing as soon as the flour is just combined, about 20 seconds. The dough will be soft.

Stuff and Roll the Cookies

Scoop the dough using a 1.5-ounce ice cream scoop (about 3 tablespoons) onto a parchment-lined baking sheet or a large plate.

Break the dark chocolate into small pieces. Press the pieces firmly into the top of each dough ball.

Use your hands to pull the dough up and over the chocolate, rolling it into a ball so the chocolate is completely covered.

This step is important; if the chocolate isn’t fully enclosed, it can leak out during baking.

Roll each stuffed cookie dough ball in the fennel sugar mixture until it’s evenly coated.

Chill and Bake

At this point, you can freeze the cookies. Place the plate in the freezer until the dough balls are solid, then transfer them to a freezer bag for up to 3 months.

If baking right away, place the cookies you want to bake on a parchment-lined baking sheet, leaving at least two inches between each one.

Bake for ~10 minutes (or ~12 minutes from frozen).

You want to pull these when they are slightly underbaked rather than overbaked. Look for the edges to be set and just turning golden brown, while the center is still puffed and looks a bit greasy.

Sprinkle with a little extra fennel sugar if you want. Let the cookies cool on the baking sheet for ~15 minutes before moving them to a wire rack to cool completely.

Print Pin

Fennel Sugar Cookies with Dark Chocolate

The main flavor in these cookies comes from toasting whole fennel seeds and grinding them directly into the rolling sugar. This gives an otherwise simple, soft sugar cookie a grassy, anise-like flavor that works well against the bittersweet dark chocolate stuffed in the center. You can make them without the chocolate, but the stuffing helps balance the sweet fennel sugar.

Prep Time 25 minutes mins

Cook Time 10 minutes mins

Chill Time 15 minutes mins

Total Time 50 minutes mins

Ingredients

For the Fennel Sugar

• ▢ 1/4 cup granulated sugar
• ▢ 1 tablespoon whole fennel seeds

For the Cookie Dough

• ▢ 3/4 cup granulated sugar
• ▢ 1/2 cup packed light brown sugar
• ▢ 1 cup unsalted butter 2 sticks, at room temperature
• ▢ 1 vanilla bean or 2 teaspoons vanilla extract
• ▢ 1 large egg at room temperature
• ▢ 2 1/4 cups all-purpose flour
• ▢ 1/2 teaspoon baking powder
• ▢ 1/4 teaspoon baking soda
• ▢ 1/2 teaspoon salt
• ▢ 3.5 oz dark chocolate (70% or higher) 100 g

Instructions

• Toast fennel seeds in dry pan until fragrant, about 1 minute.
• Grind fennel seeds and mix with sugar to create fennel sugar.
• Cream butter and sugars in mixer for 4 minutes until fluffy.
• Add vanilla and egg, mix for 1 minute.
• Whisk dry ingredients separately, then mix into butter mixture briefly.
• Scoop dough and press chocolate pieces into center of each ball.
• Roll dough balls to enclose chocolate completely.
• Coat each ball in fennel sugar.
• Place on parchment-lined baking sheet with 2 inches between cookies.
• Bake at 350°F for 10 minutes until edges are golden but center is soft.
• Cool on baking sheet for 15 minutes before transferring to wire rack.

Notes

Can freeze unbaked cookies for up to 3 months. Optional extra fennel sugar sprinkle after baking.