2 tablespoons confectioners' sugar, plus more for sprinkling
1/8 teaspoon salt
1/8 teaspoon ground cinnamon
1/2 cup (1 stick) cold unsalted butter, cut into small pieces
1/4 cup granulated sugar
1 teaspoon pure vanilla extract
1 large egg
1/2 cup Raspberry jam
Sift flour and baking powder into a bowl; set aside. Pulse pecans, confectioners' sugar, salt, and cinnamon in a food processor until finely ground (but not wet); transfer to the bowl of an electric mixer fitted with the paddle attachment.
Add butter and granulated sugar; mix on medium speed until fluffy. Mix in vanilla and egg. Reduce speed to low. Add flour mixture; mix until combined. Halve dough; shape into disks. Wrap in plastic; refrigerate until firm, at least 2 hours.
Preheat oven to 375 degrees. Working with 1 disk at a time, roll out dough on a lightly floured surface to 1/8 inch thick. Refrigerate 20 minutes. Cut out squares with a 2-inch fluted cutter. Cut out centers of half the squares with a 1/2-inch heart cutter; re-roll scraps. Space 2 inches apart on parchment-lined baking sheets. Bake squares and hearts until pale golden, 8 to 10 minutes. Transfer to racks to cool.
Sprinkle cutout cookies with confectioners' sugar. Spread jam onto uncut squares; top with cutout ones. Store in an airtight container up to 2 days.