Chocolate-Butterscotch Icebox Cake

Step 1

In the bowl of an electric mixer, cream butter and sugar together until fluffy. Add egg yolk, milk and vanilla extract; mix until smooth. Whisk together baking powder, salt, flour and cocoa, then add to mixer bowl and mix until combined. Roll into a 10-inch-long log, wrap in plastic wrap or parchment paper and chill for at least 1 hour and up to 3 days.

Step 2

Heat oven to 350 degrees. Slice dough into 1/8-inch rounds and place on parchment-lined baking sheets. You should have about 48 cookies. Bake for about 12 minutes, rotating the sheets halfway through. Remove from oven and let cool.

Step 3

In a medium saucepan over medium heat, combine brown sugar, maple syrup, butter and salt. Stir continuously until mixture is combined and sugar is dissolved. Continue cooking without stirring until mixture bubbles, about 5 minutes. Remove from the heat and stir in 1/2 cup cream, then stir in bourbon. Let butterscotch cool completely.

Step 4

In the bowl of an electric mixer, combine remaining 3 cups cold cream and the butterscotch. Whisk until stiff peaks form, 2 to 3 minutes.

Step 5

Divide wafers into six batches, about eight cookies per batch. On a serving platter, arrange one batch of cookies into a heart shape, breaking into pieces to fill in gaps if necessary. Top wafers with about 11/4 cups butterscotch cream, smoothing into a heart shape with an offset spatula. Repeat layers until cookies and cream are finished, ending with a layer of cream. (There may be extra cookies and cream; build the cake higher if you like.) Cover with plastic wrap and chill cake in the refrigerator until cold, at least 1 hour, before decorating the top.

Step 6

Melt the chocolate in a heatproof bowl set over a pot of simmering water. Stir in coconut oil. Let chocolate cool until lukewarm but still fluid. Drizzle over cold cake. Return cake to the refrigerator and let sit overnight or up to 2 days before serving.