With a mixer on medium speed beat the butter and cream cheese together until smooth and blended.
Add granulated sugar and vanilla and beat until combined.
Reduce mixer speed to low and gradually add the flour, beating until a cookie dough forms.
Wrap the cookie dough in plastic wrap and refrigerate 30 minutes until just chilled.
While the dough is chilling, preheat the oven to 375F. Line a baking sheet with parchment paper.
Divide dough into 24 pieces, each about one tablespoon of dough, and roll into balls.
Arrange each cookie ball on prepared baking sheet at least 1-inch apart. You will probably need to bake the cookies in two batches.
Using your thumb or the back side of a rounded measuring spoon, make an indentation in the center of each cookie dough and fill with raspberry preserves, about ½ teaspoon in each center.
Bake until the edges are golden, about 12 minutes. Repeat with remaining cookie dough.
Let cookies stand on the baking sheet for 2 minutes then transfer to a wire rack and cool completely.
For the glaze, in a small bowl combine confectioners sugar and milk, stirring until smooth and blended.
Transfer to a piping bag, or using a fork, drizzle the glaze over the cooled cookies.