Preheat your oven to a gentle 325°F (160°C). Line a couple of baking sheets with parchment paper.
In a stand mixer (or using a hand mixer with a large bowl), combine the softened butter, sifted powdered sugar, salt, and vanilla. Beat these together until the mixture is beautifully light and fluffy – this usually takes about 3 minutes.
Gradually add the sifted all-purpose flour to your creamy mixture. Mix on low speed until everything is just combined and a soft, cohesive dough starts to form. Be careful not to overmix!
Gently take the dough out of the mixer and briefly knead it with your hands for about one minute until it forms a smooth ball.
Wrap the dough ball tightly in plastic wrap and pop it into the fridge for at least 30 minutes. This quick chill makes the dough firm and much easier to roll out neatly.
On a lightly floured surface (and dusting your rolling pin too!), roll out the chilled dough to an even thickness of about ¼ inch. If it starts to stick, add a little more flour.
Grab a 3-inch round cookie cutter and cut out as many circular shapes as you can. Gather any dough scraps, gently re-roll them, and cut out more circles until all the dough is used.
With half of your cut-out circles, use a smaller 1½-inch cookie cutter (like a star, heart, or even a mini circle) to cut a shape from the very center. These will be your top cookies!
Carefully arrange both the whole and the cutout cookies on your parchment-lined baking sheets. Bake for 15-20 minutes, or until the edges just begin to turn a very light golden color. For even baking, rotate and switch the pans halfway through.
Once baked, remove the cookies from the oven and let them cool completely on a wire rack. They'll be delicate when warm!
Take the fully cooled whole cookies and spread a thin, even layer of your delicious raspberry jam on the flat bottom side of each.
Lightly dust the cutout cookies (the ones with the hole in the middle) with a sprinkle of powdered sugar. Then, gently place one sugar-dusted cutout cookie on top of each jam-covered whole cookie, making sure the jam "peeks through" the hole. Enjoy your beautiful and tasty homemade treats!