- 2 1/3 cups all-purpose flour*
- 1 teaspoon baking powder
- 3 large egg yolks
- 1/2 cup Imperial Sugar Extra Fine Granulated Sugar
- 2 teaspoons vanilla extract
- 1/2 teaspoon salt
- 2 sticks (1 cup) unsalted butter, super soft but not melted
Dark Chocolate Filling
- 3/4 cup whipping cream
- 2 tablespoons Imperial Sugar Extra Fine Granulated Sugar
- 6 ounces best chocolate, about 55% cocoa
- Halloween sprinkles, as needed
Orange Chocolate Filling
- 12 ounces white chocolate
- 2 tablespoons vegetable oil (any kind)
- A few drops red gel type food color
- A few drops yellow gel type food color
- *Spoon & Sweep method: Use a spoon to fill measuring cup with flour until required amount is obtained. Scooping measuring cup directly into flour bag will firmly pack flour resulting in too much flour required for recipe.
- Sift together flour and baking powder. Set aside.
- In a bowl large enough to hold all ingredients mix egg yolks until well combined. Add sugar and very quickly whisk together. Using whisk, whip for 3 minutes until mixture is pale and well-doubled in volume.
- Add vanilla and salt.
- Add soft butter to flour mixture and either stir with a rubber spatula or use hands until dough forms.
- Press dough onto a plastic food film lined cookie sheet and place in freezer until firm enough to roll. Alternatively chill overnight in refrigerator.
- For dark chocolate filling, bring whipping cream and sugar to a full boil. Remove from heat and quickly whisk in chocolate until completely smooth. Cover with plastic food wrap and set aside.
- If orange chocolate filling is desired, it is made after cookies are baked in step 14.
- Preheat oven to 350°F. Set aside 2 cookie sheets lined with parchment paper.
- Dough will stick minimally if rolled on lightly floured parchment paper. Roll dough about 1/8-inch thick. It’s important that dough is rolled evenly thick.
- Cut in pumpkin or round shapes and place on prepared sheets. Cookies will not spread much.
- Place in oven and bake until a few edges turn barely golden, about 9-10 minutes depending on thickness.
- If desired, Step 12 can be skipped over, and eyes and mouth can be piped onto cookies once filled (Step 18). Procedure for cookies shown in photograph: Half of cookies are cut while still warm. Cut eyes and mouth using a sharp paring knife or X-Acto knife. Do not push cut dough out of eyes and mouth as warm cookies are too fragile to do so.
- When cookies are completely cold, gently lift cookies and remove excess crumbs from eyes and mouth.
- For orange chocolate filling, combine white chocolate and oil in a microwave safe bowl. Heat in 10 second increments in microwave oven until melted. Add a few drops red and yellow food gel to create orange. Before filling, chocolate should have same consistency as ketchup. Cool or heat if necessary and if needed add a touch more oil. Jump to Step 16.
- Dark chocolate filling should have similar consistency of ketchup to sandwich cookies. If needed, chill briefly or heat just a tiny bit. If overheated, it can be chilled and vise versa.
- Cookies must be completely cold before filling. Spoon a generous tablespoon of chocolate filling on non-cut cookie. Top with a cut cookie and gently press until chocolate pushes through eyes and mouth and reaches edge.
- After a few sandwiched cookies, chocolate filling will be firm enough for Halloween sprinkles to be applied. Hold a sandwiched cookie and press sprinkles on edge.
- For cookies that were not cut prior to filling, melt 1/4 cup dark or white chocolate in 10 second increments in microwave. If chocolate is very thick, it can be thinned by adding a 1/2-1 teaspoon vegetable oil. White chocolate is made orange by adding a drop red and a drop yellow gel food color. Place chocolate in a small piping tip and decorate eyes and mouth on surface of cookies.