12 Days of Christmas Cookies: #7 Boston Cream Pie Cookies

(This recipe is a repost from The List.)

These cookies are for Em, who challenged me to come up with a Boston cream pie cookie. Ta-dah...I did it!

When I wrote this recipe, I thought a lot about Boston cream doughnuts. The doughnutty part is airy and chewy, but its flavor is pretty light because the doughnut itself is really just a delivery system for the custard filling and chocolate glaze. Simple enough, right?

So I got to work on a cookie base that would have a good texture and a yummy flavor but that wouldn't steal the show from the headlining duo. The solution? An oatmeal sugar cookie as the delivery system. (Stay tuned for more holiday-themed creations that use my oatmeal sugar cookie recipe as a base.)

Real Boston cream pie is filled with custard, but I used store-bought instant vanilla pudding instead because I wasn't sure if real custard would be stable enough--or thick enough--to hold up in the oven. (And because I've only made custard once or twice before and didn't want to risk it.) I also used 1/2 cup less milk than the package instructions called for so that the pudding would be thick and sturdy. (There's nothing worse than a filled/stuffed cookie whose filling/stuffing "bleeds out" in the oven.) Though I made a thickened pudding mixture, I wasn't convinced that it would hold up as the center of a stuffed cookie. So I decided to use the pudding as the filling for a thumbprint cookie instead.

A Boston cream pie wouldn't be Boston cream pie without the chocolate topping, of course. I decided to use semisweet chocolate chips that I melted over a double boiler. I then dipped the baked, cooled cookies, top-sides down, in the chocolate.

Makes 21 cookies. (To see this recipe in process, check out Picturing Boston Cream Pie Cookies.)

Thumbprint Filling

1 pack (1 ounce) instant vanilla pudding 1 1/2 cups milk 1 teaspoon vanilla

Creamables	1 stick butter 1 cup white sugar
Wet Ingredients	1 egg 2 teaspoons vanilla
Dry Ingredients	1 1/4 cups finely ground oatmeal 1 1/4 cups flour 1/2 teaspoon baking soda 1/4 teaspoon salt
Glaze	1 1/4 cups chocolate chips, melted

1. In a small bowl, make the pudding. Use 1/2 cup less milk than the box instruction call for, and add 1 teaspoon of vanilla. Put the pudding in the refrigerator to cool until Step 10.
2. Preheat oven to 350º.
3. In your Kitchen Aid or a large mixing bowl, cream together the creamables.
4. In a small bowl, combine the wet ingredients. Whisk together until smooth.
5. Add the combined wet ingredients to the creamables. Mix together until well incorporated.
6. In a large mixing bowl, add the dry ingredients. Using a spatula, fold together until evenly distributed.
7. Slowly add the dry ingredients to the combined creamables and wet ingredients. Mix until evenly combined.
8. Shape dough into balls--about 2 tablespoons each.
9. Place the  dough balls about 2 inches apart on Silpat- or parchment paper-lined cookie sheets.
10. Use your thumb to make an indentation in each dough ball. Fill each indentation with about 1/2 teaspoon of the thumbprint filling.
11. Bake at 350º for 10-12 minutes, or until golden brown. Remove the cookie sheets from the oven and let stand for 2 minutes. Then place cookies on wire racks to cool.
12. Melt 1 1/4 cups chocolate chips in the microwave or over a double boiler. Dip the tops of the cooled cookies into the chocolate. Return the cookies to the wire racks so that the chocolate cools and solidifies.