Makes 36 cookies
packed light brown sugar
all-purpose flour, spooned and leveled, plus more for the work surface
(2 sticks) unsalted butter, at room temperature
pure vanilla extract
12-ounce jar raspberry jam
- Heat oven to 350° F. Spread the almonds on a baking sheet and toast, tossing occasionally, until fragrant, 6 to 8 minutes; let cool.
- In a food processor, process the almonds and ¼ cup of the brown sugar until the almonds are finely ground.
- In a medium bowl, whisk together the flour, baking powder, salt, and cinnamon.
- Using an electric mixer, beat the butter and the remaining ¼ cup brown sugar on medium-high speed until fluffy, 2 to 3 minutes. Beat in the egg and vanilla. Reduce speed to low and gradually add the almond mixture, then the flour mixture, mixing until just combined (do not overmix).
- Divide the dough in half, shape into two disks, wrap in plastic wrap, and refrigerate until firm, at least 3 hours.
- Heat oven to 350° F. On a lightly-floured surface, roll out each piece of dough to a ⅛-inch thickness. Using a 2- to 2 ½-inch round cookie cutter, cut the dough into rounds and place on parchment-lined baking sheets, spacing them 1 inch apart. Using a ¾- to 1-inch round cookie cutter, cut out the centers from half of the cookies. Reroll and cut the scraps as necessary.
- Bake, rotating the baking sheets halfway through, until the edges are golden, 10 to 12 minutes. Cool slightly on the baking sheets, then transfer to wire racks to cool completely.
- Sprinkle the confectioners’ sugar on the cookies with the holes. Spread 1 teaspoon jam on the remaining cookies and top with the sugared cookies. Store the cookies in an airtight container at room temperature for up to 5 days.