Raspberry Chocolate Sandwich Cookies

To make cookie dough, whisk together flour, cocoa powder, baking soda, and salt in a bowl and set aside.

Gently melt chocolate in a double boiler or microwave (use 50% power in 20 second increments) until just melted. Set aside to cool slightly.

Place butter and sugars in the bowl of a stand mixer fitted with the paddle attachment. Beat on medium-high speed until lightened and somewhat fluffy, about 2 to 3 minutes.

Reduce mixer speed to low and add eggs, one at a time, mixing until each egg is completely incorporated before adding the next. Scrape down the beater and the sides of the bowl, then increase speed to medium high for 30 seconds until slightly lightened in color.. Mix in vanilla.

Pour in lukewarm cooled chocolate and mix on low speed, scraping the sides and bottom of the bowl well, until batter is uniform in color. Add dry ingredients and mix on low speed until just incorporated.

Press a layer of plastic wrap on the surface of the dough. Refrigerate for 20 to 30 minutes or until it's just firm enough to work with.

Meanwhile, preheat oven to 350 degrees F. Line two baking sheets with parchment paper.

Scoop rounds of dough using a small cookie scoop (about 20g, or 1 tablespoon-ish of dough per cookie). Flatten dough balls slightly into a puck shape (this will help it spread more evenly). Leave 2-3 inches of space between cookies as they will spread quite a bit.

Bake for about 8 minutes or until tops are puffed and no longer shiny.

Remove from oven and immediately swirl a round cookie cutter (slightly larger than the diameter of the cookie) around each still-soft cookie to tuck in any rough edges and perfect the circular shape. Let cool on sheets for 10 minutes, then transfer to a wire rack to cool completely. Repeat with remaining dough (you should end up with about 44 individual cookies).

To make ganache, (and you can start this while the cookies are baking since it'll take a little while to cool), place chopped chocolate in a heat proof bowl. Warm cream in a small saucepan until it just begins to bubble around the edges (do not let it boil). Pour over chopped chocolate. Let sit for 30 seconds then slowly whisk, working from the center outward in concentric circles until an emulsion forms. Continue to gently whisk until cream is fully incorporated and chocolate is melted. 

Let cool, gently whisking every 10 minutes or so, until ganache is thickened to the consistency of peanut butter. This will take about 45 minutes at cool room temperature, or you can refrigerate (gently whisking every 5 to 10 minutes to ensure it cools evenly) to speed it up a bit. Transfer to a piping bag fitted with a 1/2-inch round tip. Transfer raspberry jam to another piping bag with a 1/4-inch round tip (you can also spoon the jam into the centers).

Pair up the cookies in matching sizes and arrange on baking sheet with one cookie in each pair flipped upside down. Pipe a ring of ganache on the flat undersides of half of the cookies. Fill the center of ring with a teaspoon or so of raspberry jam. Lightly press a second cookie on top (don't press too hard or the filling will squeeze out). Refrigerate until fully set and ready to serve.

Cookies will keep, refrigerated in an airtight container, for up to one week.