Dark chocolate, vanilla bean caramel and buttery chocolate shortbread cookies are the three components that make up these Chocolate-Dipped Chocolate Caramel Sandwich Cookies. They’re definitely a cut above your average cookie, with three components that are incredibly delicious on their own and even better when they’re combined. They do take a little extra effort to put together, but you can’t beat these when you are looking for a special cookie to make for your favorite chocolate lover or to serve for a special occasion.
The shortbread cookies are the base of the sandwich. They are very tender, with a melt-in-your-mouth kind of a texture, and a mild chocolate flavor. The dough is easy to make in the food processor, so even though you need to allow the dough to chill, making the cookies is actually a very quick process. While crispy cookies might sound good, the caramel filling in these cookies is very soft and would simply squish out from between the cookies if they were hard and crunchy. Tender cookies meld with the filling seamlessly, so you get cookie and caramel in each bite. I used a heart-shaped cutter for this batch, but you could use a plain round cutter or any other shape that you have on hand.
The caramel is velvety smooth and soft, with a hint of chewiness to it. You really taste a lot of vanilla, which gives it a wonderful floral quality and a surprising lightness. It is much thicker than a caramel sauce, but it doesn’t firm up the way that, say, an individually wrapped caramel might. It’s easy to work with as a filling for sandwich cookies like these because it can actually be spread in between the cookies. Like other thick, soft caramels, however, it can ooze out the sides if you end up trying to pack too much filling into each sandwich. If you’re looking for a shortcut, you can use storebought caramels to make the filling for these cookies. They will need to be softened slightly in the microwave before you can place them between the cookies as a filling, but they are firmer and easier to work with than this caramel. They will have a firmer, chewier consistency to them than the homemade caramel.
The finishing touch for these cookies is, of course, dipping them in chocolate. The chocolate coating keeps the caramel filling in place and makes these cookies look spectacular. You need to temper your chocolate and use quite a bit of it. I used about 16-20 ounces of dark chocolate to dip the cookies, since a deeper bowl of chocolate is a lot easier to work with and keep warm while you dip every cookie. Leftover chocolate can be poured out and allowed to solidify after you’re done working, and it can then be reused the next time, so nothing will go to waste even if it seems like you have a lot of chocolate in use at once! Again, if you want to save a little time (and chocolate), you can take a shortcut by placing the cookies on a cooling rack and simply pouring a little chocolate over the top of each to cover it entirely. The bottoms can be dipped later. This method is a little quicker, but it is messier, so I prefer to dip them one by one.
It takes more time to make these than your average batch of cookies, but they are fantastic and well worth the effort. They’re almost like a homemade candy bar in terms of flavors and textures, and that is something well worth spending a little extra effort on!
Chocolate-Dipped Chocolate Caramel Sandwich Cookies
1 3/4 cups all purpose flour
1/4 cup cocoa powder
2/3 cup confectioners’ sugar
1/4 tsp salt
3/4 cup butter, cold
1 tsp vanilla extract
1 large egg
1 batch Soft Vanilla Bean Caramel (recipe below), for filling (not all will be used)
approx 16-oz dark chocolate, for dipping (not all will be used)
Combine flour, cocoa powder, confectioners sugar and salt in the bowl of a food processor. Pulse to combine. Add butter and pulse until mixture is sandy. Add in vanilla extract and egg and process until dough comes together.
Divide the soft dough into two balls and wrap each in plastic wrap, flattening it into a disc about 1/2 inch thick. Refrigerate for 30-45 minutes.
Preheat oven to 325F.
Working with one disc of dough at a time, roll the dough out onto a lightly floured surface until it is no more than 1/4 inch thick. Cut out hearts (or circles) using a 2-inch cutter. Place onto a parchment-lined baking sheet.
Bake cookies for 9-10 minutes, until cookies are firm on the edges.
Repeat with remaining dough.
Allow cookies to cool completely on a wire rack.
Pair up the cookies. Fill each pair with a generous amount of caramel sauce, spreading it to the edges of the cookies. Be careful not to squish too much caramel out from between the cookies as you sandwich them.
Place cookies on a baking sheet and chill in the freezer for 15 minutes to set the caramel in place.
Meanwhile, temper your chocolate and transfer to a deep bowl. Set a clean piece of parchment paper on the counter.
Dip cookies thoroughly and place on prepared parchment paper. Allow chocolate to set up before serving or storing in an airtight container.
Makes 36 cookies (18 sandwiches)
Soft Vanilla Bean Caramel
adapted from Chocolates and Confections
3 1/2 oz water
9 oz sugar
1/2 vanilla bean
6 1/2 oz sweetened condensed milk
7 1/2 oz corn syrup
3 1/2 oz butter, softened
1/2 tsp salt
In a medium saucepan, combine water and sugar. Split the vanilla bean lengthwise and scrape out the vanilla bean seeds using the back of a knife. Add to sugar. Cook over medium heat, stirring constantly, until the sugar dissolves. Bring mixture to a boil. Add in sweetened condensed milk and corn syrup and cook, stirring regularly, until caramel comes to 230F.
When the caramel reaches 230F, add in the butter. Continue to cook while stirring to dissolve the butter and cook until temperature reaches 250F. Remove from heat and stir in the salt.
Pour into a large bowl and allow the caramel to cool to room temperature before using.
Advanced: For the advanced method, pour the caramel out into buttered 9×9-inch square baking sheet that is lined with parchment paper and allow it to set. Chill the caramel in the freezer for 20 minutes once it reaches room temperature, then run a knife around the edges of the caramel and pop it out of the pan onto another sheet of parchment paper. Remove the base sheet of parchment.
Use your heart-shaped cookie cutter to cut out pieces of caramel and place them between the cookies. When all cookies have been assembled, allow them to sit at room temperature for 20-30 minutes to set the caramel layer. Then, chill cookies for about 15 minutes in the freezer before dipping them.