Raspberry Shortbread Sandwiches

In a bowl, with a mixer on medium speed, beat butter, granulated sugar, and vanilla until smooth. Add flour and salt and mix on low speed until dough comes together in a ball. Transfer to a lightly floured surface.
Divide dough in half. With a lightly floured rolling pin, roll each portion to about 1/8 inch thick. With a floured 2- to 3-inch round or star-shaped cutter, cut out cookies. If desired, cut a 1/2-inch circle out of the center of half of the cookies to make a window for the jam filling (see notes). Place cookies 1 inch apart on buttered 12- by 15-inch baking sheets. Gather excess dough into a ball, reroll, and cut out remaining cookies.
Bake in a 325u0b0 regular or 300u0b0 convection oven until edges are just beginning to brown, 10 to 12 minutes. If baking more than one sheet at a time in one oven, switch positions halfway through baking. Transfer cookies to racks to cool completely.
Spread the flat side of each of half the cookies (those without holes) with about 1/2 tablespoon jam. Top each with a remaining cookie (with a hole), flat side toward filling. Sprinkle tops of cookies evenly with powdered sugar.
Nutritional analysis per sandwich cookie.
Use a sharp knife, a 1/2-inch cookie cutter, or the narrow end of a 1/2-inch plain pastry tip to cut holes out of half the cookies before baking. These cookies are best eaten the day they are filled, but you can store cooled, unfilled cookies airtight at room temperature up to 3 days; freeze to store longer.