Steps:
- Whisk flour cocoa powder, baking powder , and 1 tsp salt in a medium bowl to combine.
- Beat granulated sugar and butter in a bowl of a strand mixer fitted with paddle attachment on medium-high speed until light and fluffy, about 4 minutes.
- Add egg and vanilla and beat to incorporate, about 1 minute.
- Reduce speed to low and add dry ingredients. Beat just until dough comes together.
- Divide in half and pat each into a disk, wrap tightly in plastic. Chill just long enough that dough is rollable and no longer sticky, about 30 minutes.
- Working one at a time, roll out dough between 2 sheets of parchment paper until 1/8" thick. Slide onto baking sheets, still sandwiched between parchment, and chill until very firm, about 1 hour.
- Place racks in upper and lower thirds of oven, preheat to 350 degrees.
- Carefully peel away top sheets of parchment from dough and punch out cookies with larger cutters. Punch out centers of half of cookies with smaller cutters.
- Carefully transfer whole coolies with a spatula to a parchment-lined baking sheet, spacing 1" apart.
- Sprinkle remaining cutout cookies with sanding sugar, then transfer to another parchment-lined baking sheet.
- Bake coolies until edges are set, 7-10 minutes. Let cool on baking sheets.
- Repeat process with scraps (chill dough again before punching out shapes).
- Melt chocolate and tahini in a bowl in a microwave in 20-second bursts, stirring after each, until chocolate is melted (or melt in a heatproof bowl set over a saucepan of simmering water, do not let bowl touch water). Stir to combine and season with salt.
- Spread filling over whoe cookies ; top with cut-out cookies.
- DO AHEAD: Cookies can be assembled 5 days ahead. Store airtight at room at room temperature.
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