Assorted Dessert Squares And Cookies Recipe

Make shortbread dough

Preheat oven to 350°F (175°C). In a large bowl, cream 1 cup softened unsalted butter and 1/2 cup granulated sugar until light and fluffy (about 2–3 minutes). Mix in 1 tsp vanilla. Add 2 cups all-purpose flour and 1/4 tsp salt and mix on low until just combined and a soft dough forms.

Bake base

Press the dough evenly into the bottom of a 9x13-inch pan lined with parchment leaving edges slightly higher if desired. Use a spatula or the bottom of a flat measuring cup to press firmly. Prick the surface lightly with a fork. Bake 15–18 minutes until edges are just golden. Remove from oven and let cool in pan while preparing fillings. This shortbread base will be used for the chocolate caramel squares; reserve any extra dough for thumbprint cookie assembly if desired.

Prepare caramel layer

In a medium saucepan over medium heat, combine 14 oz sweetened condensed milk, 1/2 cup packed brown sugar, 2 tbsp unsalted butter, and 1 tbsp corn syrup. Stir constantly until mixture comes to a gentle boil, then reduce heat to low and simmer, stirring, for 6–8 minutes until thickened and caramel-colored. Remove from heat.

Assemble and bake

Pour the hot caramel evenly over the cooled shortbread base and spread to an even layer. Return the pan to the oven for 5–7 minutes to set the caramel slightly. Remove and let cool 10 minutes.

Chocolate topping

Place 1 cup semi-sweet chocolate chips and 2 tbsp heavy cream in a heatproof bowl. Microwave in 20-second bursts, stirring between bursts, until smooth (or melt over a double boiler). Spread melted chocolate evenly over the caramel layer. If using, sprinkle 1/2 tsp sea salt flakes on top. Chill the pan in the refrigerator for at least 1 hour to fully set. Once set, cut into about 12 squares. Keep refrigerated or at cool room temperature for up to 4 days.

Make cookie dough

Preheat oven to 350°F (175°C) and line two baking sheets with parchment. In a bowl, cream 3/4 cup softened unsalted butter with 1/2 cup granulated sugar until light and fluffy (2–3 minutes). Beat in 1 egg yolk and 1/2 tsp vanilla until combined. Add 2 cups all-purpose flour and 1/4 tsp salt and mix until a soft, slightly crumbly dough forms that holds together when pressed.

Form and fill

Roll dough into 1-inch balls (about 1 tablespoon each) and place 1 inch apart on prepared sheets. Use your thumb or the back of a 1/2-teaspoon measuring spoon to make an indentation in the center of each ball. Fill each indentation with about 1/2 teaspoon jam (total ~1/2 cup jam).

Bake

Bake 12–14 minutes until the edges are very lightly golden. Cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely. Store in an airtight container for up to 5 days.

Mix dry and wet

Whisk together 1.5 cups all-purpose flour, 1/2 cup unsweetened cocoa powder, 2 tsp baking powder, and 1/4 tsp salt in a medium bowl. In a separate large bowl, whisk 1 cup granulated sugar, 1/4 cup vegetable oil, 2 eggs, and 1 tsp vanilla until smooth and glossy.

Combine and chill

Add the dry ingredients to the wet and stir until a soft, slightly sticky dough forms. Cover and refrigerate the dough for 30 minutes — this firms it and helps create the crackled surface.

Form and bake

Preheat oven to 350°F (175°C) and line baking sheets with parchment. Place 1/2 cup powdered sugar in a bowl. Scoop about 1.5 tablespoons of chilled dough, roll into a ball, and coat thoroughly in powdered sugar. Place on the sheet 2 inches apart. Bake 10–12 minutes until the tops are cracked and the cookies are set but still slightly soft in the center. Cool on the sheet for 5 minutes, then transfer to a rack to cool completely.

If desired, drizzle melted chocolate (about 2 tbsp) over thumbprint cookies or crinkle cookies for decoration. For the chocolate caramel squares, you can add a sprinkle of sea salt or a short drizzle of extra melted chocolate after cutting. Arrange the assorted squares and cookies on a platter: cut chocolate caramel into squares (about 12), place jam thumbprints (about 18) and crinkle cookies (about 18) together. Store in an airtight container; keep the chocolate caramel squares chilled if the caramel is very soft.