Place the all-purpose flour, granulated sugar, and salt in the bowl of an electric mixer. Blend briefly until the dry ingredients are evenly combined.
With the mixer operating on low speed, incorporate the softened butter gradually, adding one 1/2-inch piece at a time. Continue mixing for approximately 1–2 minutes, until the mixture develops a crumbly appearance with a slightly moist texture.
Add the vanilla extract and softened cream cheese. Mix on low speed for about 30 seconds, stopping as soon as the dough begins to gather into large clumps.
Turn the prepared dough out onto a countertop and divide it into two equal portions. Shape each portion into a disk measuring approximately 4 inches across.
Securely wrap both disks in plastic wrap and refrigerate for 20–30 minutes, or until the dough has started to firm.
Preheat the oven to 375°F (190°C). Line a baking sheet with parchment paper.
Remove one chilled dough disk from the refrigerator. On a lightly floured work surface, roll the dough evenly to a thickness of about 1/8 inch.
Cut the dough into shapes using cookie cutters of your choice. From half of the cutouts, remove a smaller shape from the center; these pieces will form the upper halves of the sandwich cookies.
Arrange the cut cookies on the prepared baking sheet, leaving roughly 1 1/2 inches of space between them.
Repeat the rolling and cutting procedure with the remaining chilled dough disk.
Bake the shaped cookies at 375°F (190°C) for 8–10 minutes, until their edges become lightly golden.
Turn the baking sheet around halfway through the baking period to encourage even browning.
Leave the baked cookies on the baking sheet for 1–2 minutes before carefully transferring them to a wire cooling rack. Allow them to cool completely before assembling.
Spread a thin, even coating of raspberry jam over the flat underside of each solid cookie.
Position one cookie with a center opening over each jam-covered base, pressing very gently to create a sandwich without forcing out the filling.
Finish the assembled cookies with confectioners’ sugar, if desired.