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For the ganache:
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Gently heat cream and chocolate together in a saucepan over low heat; stirring and heating until completely smooth and combined. Cover and chill for 30 minutes (or make the ganache several hours in advance and let it sit at room temperature until it reaches the proper spreading consistency).
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For the cookie dough:
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In the bowl of a stand mixer fitted with a BeaterBlade or paddle attachment, beat the butter on medium high speed for 30 seconds. Add sugar, baking powder, and salt; beat until combined. Add egg and vanilla; beat to combine. Add flour and cocoa powder; mix until incorporated. Wrap dough with plastic wrap and chill for 1-3 hours.
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Preheat oven to 375 F. Roll dough to 1/8-inch thickness between two layers of wax paper. Cut out desired shapes. I cut the cookie shapes using a scalloped cutter. Keep the bottom half of each sandwich cookie plain. You want to make half of the cookies plain and half decorated for the top. For the top half of each cookie, use something small and round and make a slight indentation for a border. Then use a straw to make two button holes. See related blog link for step-by-step photos.
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Place cookies 2-inches apart on a silicone mat- or parchment-lined sheet pan. Bake for 8 minutes or until edges are set (tiny cutouts bake for 5-6 minutes). Transfer cookies to racks and cool completely.
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To assemble cookies:
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Spoon about 1 teaspoon of the ganache in the center bottom of each plain cookie and make a sandwich by adding a decorative top cookie.
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To store, place unfilled cookies in an airtight container, separating layers with waxed paper, at room temperature for 3 days or frozen for up to 3 months. Thaw and assemble just before service.
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My notes: To prevent distortion, I cut my cookie shapes while the dough is still on the waxed paper, then slide the waxed paper onto a cookie sheet and chill for at least 10 minutes before transferring the shapes to a sheet pan.
