Chocolate Caramel Shortbread Sandwich Cookies

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Millionaire’s Shortbread is shortbread topped with caramel and chocolate. I took that concept and created Millionaire’s Shortbread Cookies, which are shortbread sandwich cookies with dark chocolate, caramel, and walnuts. And they are seriously good. They taste like a mix between chocolate turtles and Twix.

When my friend Whitney (the lovely host of the Whitney Reynolds Show on PBS) invited me to her cookie party, she made it clear that this wasn’t just a cookie exchange, it was a contest. And I knew I had to win. So I dreamed up these cookies and I am excited to announce that I did win! There were 17 different cookies in total and an intense round of judging.

These cookies are extraordinary. They are equal parts beautiful and delicious. Homemade whiskey caramel is sandwiched between two thin buttery shortbread cookies that are covered in dark chocolate and topped with toasted walnuts. It’s a sophisticated take on a holiday cookie.

I love giftable desserts, and these cookies would be a memorable gift. They are easy to make in large batches making them a wonderful holiday gift for co-workers or friends, and they are a nice change from the sugar cookies that are so common during the holiday season.

While these do take a bit of effort to prepare, you could use store-bought shortbread cookies which would eliminate a good chunk of the preparation time.

You will have extra caramel sauce, but that is a good thing. Use it in other recipes, pour it over ice cream, or put it in a pretty jar and give it as a gift.

I should let you know that I tried three different shortbread recipes before settling on this one. Some of the other recipes out on the internet make shortbread that is too crumbly and won’t hold together. I think that it is essential to mix all purpose flour and semolina (which has a more course texture) and helps to give the shortbread the correct texture. I also think that you need to use powdered sugar instead of granulated. The end result is a dough that is similar in consistency to sugar cookie dough. Lastly, I want to stress the important of chilling the dough after cutting the cookies and before placing them in the oven to prevent the cookies from spreading out as they bake.

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Millionaire’s Shortbread Cookies (Shortbread Sandwich Cookies with Dark Chocolate and Walnuts)

These exceptionally delicious Millionaire's Shortbread Cookies won a Christmas cookie contest, and they are a stunning homemade holiday gift.

Prep Time 1 hour 30 minutes

Cook Time 1 hour

Total Time 2 hours 30 minutes

Ingredients

• For the Shortbread:
• 2 stick of Butter at Room Temperature it must be at room temp
• 1/2 cup Powdered Sugar
• 1 teaspoon Vanilla
• 1 1/2 cups All-Purpose Flour
• 1/2 cup Semolina
• For the Whiskey Caramel:
• 1/4 cup Whiskey
• 1 cup Brown Sugar
• 1/2 cup Butter
• 1/2 cup Heavy Cream
• 1/2 teaspoon Salt
• 1 tablespoon Vanilla
• 1 cup Melting Chocolate I used Dark Chocolate or Almond Bark
• 1/4 cup Walnuts finely chopped

Instructions

1. First, whip the butter in an electric mixer for one minute on medium speed. Then add the powdered sugar and beat for 2 minutes. Add the vanilla and mix until combined.
2. Add the semolina, continuing to mix in the electric mixer on medium speed. Then add the all-purpose flour 1/2 cup at a time. Mix until the ingredients are evenly incorporated.
3. Then divide the dough into two pieces, flatten into discs, cover with plastic wrap, and chill in the fridge for at least 1 hour.
4. While the dough is chilling, prepare the whiskey caramel sauce. Melt the butter in a saucepan over medium heat. Then add the sugar and whisk until melted.
5. Add the whiskey, salt, and vanilla. Let simmer steadily for 5 minutes, stirring frequently.
6. Add the cream, stir, and let the sauce slowly simmer and reduce for 20-25 minutes, until it has thickened. Stir every few minutes. You want the caramel to be thick enough to for a thick layer to stick on the back of a spoon. Then keep the caramel warm on the lowest setting on your stove.
7. After the dough has chilled, heat your oven to 350 degrees. Remove the dough from the oven, and let it soften just enough so that you can roll it out. Roll the dough out so that it is 1/8 of an inch thick and then cut it into squares about an inch big.
8. Place the squares of dough on a parchment-lined baking sheet and chill them for 10 minutes before baking them on a center rack in the oven for about 8 minutes. You want to bake the dough until the edges are golden brown.
9. Before you turn your oven off, toast the walnuts for 2-3 minutes.
10. Let the cookies cool completely. Then use the shortbread cookies and the caramel to make sandwiches by spooning about 1/2 teaspoon of the caramel onto a cookie and topping it with another cookie. Make the sandwiches so that the top sides of the cookies face out (those are the smooth sides and will result in a nicer looking finished product. Once you have made all of the cookie sandwiches, prepare the melting chocolate.
11. Next you need to melt the chocolate in a double boiler. Fill a pot with about 4 inches of water, and heat over medium-low heat until is steaming. You do not want the water to boil. Place a glass or metal bowl over the pot, and pour the chocolate into the bowl. Stir the chocolate until it melts.
12. Individually pick up the cookies with a fork, and dunk them in the chocolate being sure to completely coat them. Finish the cookies off by sprinkling walnuts over the top of the cookies.
13. Let the chocolate set. Place the cookies in the fridge to hurry this process along if necessary.