In a medium mixing bowl. Combine flour, cocoa, baking soda, salt, and cinnamon, stirring well with a whisk.

In a large mixing bowl using a hand mixer, cream together the granulated sugar and butter until light and fluffy. Add egg and vanilla and beat until well blended. Beating at low speed, gradually add flour mixture; beat just until a soft dough forms. Divide dough into 2 equal portions, and wrap each dough portion in plastic wrap. Chill at least 1 hour.

Preheat oven to 375 degrees F. Roll each dough portion into a 1/8-inch thickness on a lightly floured surface; cut with a 2-inch heart shape cookie cutter with fluted edges to form 48 cookies. Cut out the center of 24 of the cookies with a smaller heart shaped cookie cutter with a fluted edge. Place cookies 1 inch apart on parchment-lined baking sheets.

Bake cookies for 10 minutes. Cool on pans 5 minutes. Remove from pans; cool completely on wire racks.

Spread 1/2 teaspoon of jam on the center of each whole cookie. Place 1 cut-out cookie on top of each jam topped whole cookie. Dust with powdered sugar.