I've baked dozens of cookie recipes over the years, but this 1 recipe is most requested year over year!

These Raspberry Shortbread Cookies with Raspberry Filling and Vanilla Drizzle are a cherished delight in our family, perfect for any occasion that calls for a little homemade comfort. This recipe harks back to the sweet treats my grandmother used to make for us during the summer, using fresh raspberries picked from the farm. The combination of buttery shortbread, tangy raspberry filling, and the sweetness of vanilla drizzle makes these cookies irresistible. Whether you're planning a cozy gathering or simply want to treat yourself, these cookies are a lovely way to celebrate simple joys.

These cookies are lovely on their own with a hot cup of tea or coffee. If you're feeling indulgent, a scoop of vanilla ice cream on the side pairs beautifully with the tangy raspberry filling. For a special treat, serve them with a dollop of whipped cream and a few fresh raspberries. These cookies are also wonderful additions to a dessert platter with other classic Midwestern baked goods like apple pie or molasses cookies.

Servings: 24 cookies

1 cup (2 sticks) unsalted butter, softened
1/2 cup powdered sugar
1 teaspoon vanilla extract
2 cups all-purpose flour
1/2 cup raspberry jam or preserves
1 cup powdered sugar (for drizzle)
2-3 tablespoons milk (for drizzle)
1/2 teaspoon vanilla extract (for drizzle)

Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.

In a large bowl, cream together the softened butter and powdered sugar until light and fluffy.

Mix in the vanilla extract.

Gradually add the flour to the butter mixture, blending until the dough comes together.

Roll the dough into 1-inch balls and place them on the prepared baking sheet about 2 inches apart.

Using your thumb, make an indentation in the center of each cookie.

Fill each indentation with a small amount of raspberry jam or preserves.

Bake the cookies for 12-15 minutes or until the edges are lightly golden.

Remove the cookies from the oven and let them cool on the baking sheet for a few minutes before transferring them to a wire rack to cool completely.

To make the vanilla drizzle, whisk together the powdered sugar, milk, and vanilla extract until smooth. Adjust the consistency by adding more milk if needed.

Drizzle the icing over the cooled cookies using a spoon or a small piping bag.

Allow the drizzle to set before serving or storing the cookies in an airtight container.

For a different twist, you can use other fruit preserves like strawberry or apricot in place of raspberry. If you prefer a citrus flavor, add a bit of lemon zest to the shortbread dough. To make the cookies more festive, consider sprinkling some finely chopped nuts or decorative sugar over the top before baking. If you're short on time, you can use store-bought shortbread for a quick version of this treat.