Chocolate Wafer Sandwich Cookies with Vanilla and Chocolate Filling

I made these tasty little sandwich cookies with the February Dessert Wars challenge in mind.  The theme was dark chocolate and hearts, and I thought these cookies would work nicely.  The wafers are quite crisp, which I normally don't care for, but with the soft sweet cream filling the combination is perfect.  I did hearts for the chocolate cream filling and circles for the vanilla cream.

If you want perfectly round and heart shaped (or whatever shape you're using) wafers, you need to follow Martha's very anal instructions of chill, roll, chill, cut, chill, bake.  This ensures the dough will for the most part keep it's shape during the baking.  Both fillings were delicious, I was a little dubious of the vanilla since it uses vegetable shortening, which for some reason skeeves me out, but it was excellent, but I did prefer it chilled in the fridge so it didn't all squish out of the cookie after taking a bite.  The chocolate cream filling is simply heavenly.

Chocolate Wafer Sandwich Cookies
from Martha Stewart’s Baking Handbook

Makes about 2 dozen sandwich cookies

1¼ cups all-purpose flour, plus more for dusting
¼ cup plus 2 tablespoons Dutch-process cocoa powder
½ teaspoon baking powder
½ teaspoon baking soda
¼ teaspoon salt
1 stick (½ cup) unsalted butter, room temperature
2/3 cup packed light-brown sugar
1/3 cup granulated sugar
1 large egg
1 teaspoon pure vanilla extract

Line two large baking sheets with parchment paper; set aside. In a large bowl, whisk together flour, cocoa, baking powder, baking soda, and salt; set aside. In the bowl of an electric mixer fitted with the paddle attachment, beat the butter and both sugars on medium sped until light and fluffy, 2 to 3 minutes. Add the egg and vanilla; beat to combine. With mixer on low speed, add flour mixture, and beat to combine, scraping down the sides of the bowl as needed.
Turn out the dough onto a piece of plastic wrap, and divide in half. With floured hands, shape each piece into a flattened rectangle, wrap with plastic wrap, and refrigerate until firm, about 30 minutes.
Place one rectangle of dough on a lightly floured work surface. Roll out dough to a scant 1/8-inch thickness, stopping every so often to release the dough by running an offset spatula underneath. You should end up with a rectangle that’s about 14 by 11 inches. Transfer dough to a prepared baking sheet, and freeze until very firm, about 30 minutes. Repeat with remaining dough.
Preheat the oven to 350 degrees. Place one rectangle of dough on a clean work surface. Working quickly, cut out rounds using a 2-inch cookie cutter. (If the dough begins to soften too much, return to the freezer for a few minutes.) Using a wide metal spatula, transfer rounds to a parchment-lined baking sheets, about 1½ inches apart. Gather together remaining scraps, reroll, and cut out more rounds. Freeze until firm, about 15 minutes. Repeat with the remaining rectangle of dough.
Bake, rotating sheets halfway through, until the centers of the cookies feel firm when lightly pressed, 12 to 14 minutes. Transfer to a wire rack to cool completely.
Using an offset spatula, spread 1 tablespoon desired filling onto the flat sides of half the cookies. Sandwich with remaining cookies, keeping the flat sides down. Unfilled cookies can be kept in an airtight container at room temperature for up to 1 week. Once filled, cookies are best eaten the day they are made, but they can be kept in an airtight container in the refrigerator for up to 3 days.

Vanilla Cream Filling
Makes enough to fill 2 dozen sandwich cookies

1 1/3 (5 1/3 ounces) confectioners’ sugar
1/3 cup vegetable shortening
1/3 cup (5 1/3 tablespoons) unsalted butter, room temperature
½ teaspoon pure vanilla extract
pinch of salt

In the bowl of an electric mixer fitted with the paddle attachment, combine all ingredients. Beat on medium-high speed until fluffy and light, 3 to 4 minutes. Use immediately or refrigerate in an airtight container for up to 3 days. Let soften at room temperature before using.

Chocolate Cream Filling
4 1/2 ounces semisweet chocolate, chopped (1 cup)
3/4 ounce unsweetened chocolate, chopped
2/3 cup (half of one 14-ounce can) sweetened condensed milk
1 tablespoon unsalted butter
1 teaspoon pure vanilla extract

Melt chocolates in a heatproof bowl set over (but not touching) simmering water, stirring occasionally.  Add condensed milk, butter, and extract; stir to combine.  Continue to stir over simmering water until all ingredients are smooth, 2 minutes.  Remove from heat, and set aside to cool slightly.

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