Preheat oven to 350°F and line a cookie sheet with parchment paper or a silicon baking mat.
In the bowl of a stand mixer fitted with a paddle attachment, beat the cold butter and sugar together on medium speed until light and fluffy, about 3 or 4 minutes. Scrape down the sides of the bowl as needed.
Mix in the extract and flour until a dough forms.
Make an indent in each cookie using your thumb or a tsp measuring spoon. Fill each well with raspberry jam. The jam will flatten out as the cookies bake, so you can slightly overfill these cookies if you'd like.
Place the cookies to chill in the refrigerator for 20 minutes.
Once ready, remove from fridge and place into the oven to bake.
Bake for 15 minutes or until the edges are lightly browned.
To make the glaze, mix together all ingredients listed until there are no clumps of sugar left. You can add more or less milk (by 1/2 tsp increments) until the desired consistency has been reached.
Drizzle cookies and enjoy!