Step 1: Prepare the Dough

Begin by preheating your oven to 350°F (175°C). Line a large baking sheet with parchment paper, ensuring there's enough space for proper air circulation around each cookie.

In a large mixing bowl, cream together the softened butter and powdered sugar using an electric mixer on medium speed for 3-4 minutes, until the mixture becomes light, fluffy, and nearly white in color. This creaming process is crucial for creating the tender texture that makes shortbread cookies so irresistible.

Add the vanilla extract and mix until fully incorporated. Gradually add the flour in three additions, mixing on low speed after each addition just until the flour disappears. Overmixing at this stage can result in tough cookies, so be gentle with your dough.

Step 2: Shape and Fill the Cookies

Using your hands or a small cookie scoop, roll the dough into uniform 1-inch balls. This ensures even baking and professional-looking results. Place each ball on the prepared baking sheet, spacing them approximately 2 inches apart to allow for slight spreading.

Here's where the magic happens: using your thumb https://dearcrissy.com/raspberry-almond-shortbread-cookies/or the back of a small spoon, create a well in the center of each cookie ball. The indentation should be deep enough to hold the jam but not so deep that it breaks through to the bottom. Fill each indentation with about 1/2 teaspoon of raspberry jam, being careful not to overfill as the jam will bubble during baking.

Step 3: Bake the Cookies

Slide your Cookies into the preheated oven and bake for 12-15 minutes. Keep a close eye on them during the final few minutes – you want the edges to be lightly golden while the centers remain pale. The jam will be bubbling and fragrant when they're perfectly done.

Remove the cookies from the oven and allow them to cool on the baking sheet for 5 minutes before carefully transferring them to a wire rack. This resting period prevents the delicate cookies from breaking apart while ensuring the jam sets properly.

Step 4: Add the Vanilla Drizzle

While your cookies cool completely, prepare the vanilla drizzle by whisking together the powdered sugar, milk, and vanilla extract in a small bowl. The consistency should be thick enough to hold its shape but thin enough to drizzle smoothly. Adjust with additional milk if needed.

Once the cookies are completely cool, drizzle the icing over each cookie using a spoon or transfer it to a piping bag for more precise application. Allow the drizzle to set for at least 15 minutes before serving or storing.