Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
In a large mixing bowl, cream the softened butter and granulated sugar together until light and fluffy. This should take a couple of minutes and will help give the cookies a tender texture.
Mix in the ½ teaspoon almond extract until evenly incorporated.
Gradually add the 2 cups of flour, stirring or mixing on low just until a soft dough forms. The dough should come together and pull away from the sides of the bowl without being sticky.
Shape and fill the thumbprints
Roll the dough into 1‑inch balls and place them about 2 inches apart on the prepared baking sheet.
Use your thumb or the back of a small spoon to gently press an indentation into the center of each ball. Don’t press all the way through; you just want a well for the jam.
Fill each indentation with about ½ teaspoon of raspberry jam. Try not to overfill so the jam doesn’t overflow as the cookies bake.
Bake and cool
Bake for 12–14 minutes, or until the edges of the cookies are lightly golden and the bottoms are set. The tops should remain pale.
Let the cookies cool on the baking sheet for 5 minutes to firm up, then transfer them carefully to a wire rack to cool completely before glazing.
Prepare and drizzle the glaze
While the cookies cool, whisk together the powdered sugar, almond extract, and 2 teaspoons of milk in a small bowl. Add an extra teaspoon of milk if needed to reach a smooth, drizzleable consistency.
Drizzle the glaze over the cooled cookies in thin lines or zigzags. You can use a spoon, fork, or piping bag for more control.
Allow the glaze to set at room temperature before serving or storing.
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