Day 1 … Pretzel Caramel Shortbread

So here’s something new this year. I figure everyone could use some new holiday cookie recipes, ones with different textures and interesting flavors that may just become your family favorites. So starting today, with this post, I present to you “The Twelve Days of Cookies.” Twelve delicious cookie recipes to make your season bright. Twelve recipes that I’d never made before until I came up with this crazy idea. Twelve recipes that I started researching back in September but didn’t start testing until last week because, you know, why do something ahead when you can cram it into the last minute. As I type this, I’m not particularly happy with the last two so it’s with tightly crossed fingers that I get there. We might have to cut the advent short by two days and create a new holiday season altogether. But let’s not think about that right now. Instead let’s start with Pretzel Caramel Shortbread.

Yes: pretzels, caramel and shortbread. It’s a riff on the popular “Millionaire’s Shortbread” and it’s delicious. When I was searching around for ideas for this little project I came across Martha, of course, who had several handy dandy slideshows of beautiful holiday cookie after beautiful holiday cookie. Oh Martha, bless your heart. Buried deep in one of those slideshows was a recipe for pretzel shortbread. I was intrigued. Never one to stop at the simple, I thought it might be better topped with caramel and that might be even better topped with chocolate. Because really now, how could it not be? It had the four key cookie food groups: butter, salt, caramel, chocolate.

I looked at several recipes, took bits and pieces from a few, mashed them together with a few ideas of my own and added a shot of bourbon for good measure. Because: holidays. The result is an addictive combination of crunch, salt, butter, goo and chocolate that is hard to ignore and a pain in the butt to cut cleanly. But that’s how things go. Sometimes you have to sacrifice the pretty for the delicious (but don’t fret – I give you a few tips on how to cut pretty.)

STRESS THERAPY BAKING FACTOR: PERFECTION. First off, these are the kind of fancy cookies that are perfect for the holidays – crowd pleasing, impressive to look at, a great descriptive title and enough of an effort that you feel you’ve made something special. It’s got all the key parts of a delicious cookie: a crunchy, buttery, salty base, a rich gooey center and a dark chocolate topping accented with just a touch of flaky salt to tie it all together. While it’s a bit of a project, no single step is particularly difficult. Bring these to the cookie exchange and you’ll be the clear winner (because let’s be honest; as innocent as a cookie exhange may seem, it’s a blood sport.)

Six years ago: Pumpkin Bundt Cake
Five years ago: French Apple Tart
Four years ago: Southern Cheese Straws
Three years ago: Kale & Squash Salad
Two years ago: Apple Cider Rolls
Last year: Port Wine Cheese Log

PRETZEL CARAMEL SHORTBREAD
yield depends a lot on how you cut these. I like them on the small size, 1″x1″, which yields around 81 pieces.
note: it’s best to use a scale to weight the pretzels because they are an odd one to measure in a standard measuring cup. I recommend using the thin/small pretzel sticks and breaking them in half to make the measuring a bit easier.

for the pretzel shortbread:
3 cups salted thin/small pretzel sticks, broken in half (5 ounces)
½ cup unbleached all-purpose flour
½ teaspoon baking powder
½ teaspoon kosher salt
½ cup unsalted butter, room temperature (1 stick)
½ cup sugar
1 large egg yolk
½ teaspoon vanilla bean paste or extract

for the caramel:
½ cup unsalted butter (1 stick)
1 cup dark brown sugar
1 Tablespoon bourbon
¼ cup golden syrup, such as Lyle’s, or corn syrup
½ teaspoon flaky sea salt, such as Maldon
14-ounce can sweetened condensed milk

for the topping:
7 oz bittersweet chocolate, 65% cacao or more
1 Tablespoon vegetable oil
½ teaspoon bourbon
½ teaspoon flaky sea salt, such as Maldon

1. Preheat oven to 325° Line a 9”x9” pan with a criss-cross sling of foil, extending the edges over the pan. Spray with cooking spray and set aside.
2. For the pretzel shortbread layer: Pulse 1 ¾ cups (3 ounces) of the broken pretzels in a food processor until powdery.
3. Measure out ½ cup and place in a medium bowl (you’ll probably have leftover, discard.)
4. Whisk in the flour, baking powder and salt.
5. Transfer remaining 1 ½ cups (2 ounces) broken pretzels to food processor, and pulse a few times until coarsely chopped.
6. Measure out into 2 separate bowls, ½ cup and ¼ cup. Discard any extra.
7. In the bowl of a standing mixer fitted with the paddle attachment, beat the butter and sugar on medium speed until light and fluffy, about 5 minutes.
8. Reduce speed to low, add egg yolk, then pretzel-flour mixture, until combined.
9. With a rubber spatula, fold in the ½ cup chopped pretzels.
10. With slightly damp fingers, press the dough evenly into pan.
11. Top with the ¼ cup chopped pretzels, pressing slightly.
12. Bake shortbread until pale brown and firm in the center, 25 minutes.
13. Transfer pan to a wire rack, and let shortbread cool for 1 hour.
14. For the caramel layer: In a heavy saucepan, melt the butter, brown sugar, bourbon, golden/corn syrup, and salt together on low, then stir in the condensed milk.
15. Increase the heat to medium-low and bring the caramel to a low boil, stirring constantly with a spatula, and let it bubble for 4 minutes, or until it thickens and smells like creamy toffee. It should be thick enough for the spatula to leave a trail in the caramel for a few seconds. Don’t leave the pan or stop stirring during this step, as it can easily burn on the bottom.
16. Pour the caramel over the shortbread, then let cool completely.
17. For the chocolate layer: Melt the chocolate in a double boiler or in the microwave in 30-second bursts at 50% power, stirring between bursts.
18. Stir in the oil and bourbon until smooth then pour over the caramel, tilting the pan to evenly coat.
19. Sprinkle with the salt and let set at room temperature.
20. When the chocolate is just set, mark it into squares (I use a ruler to get the lines perfectly straight), then chill until completely firm.
21. To cut: for perfect squares, use a ruler to lightly score the chocolate. Let the bars sit at room temperature for 15 minutes to soften a bit.
22. With a serrated knife, carefully cut through the caramel layer on the pre-scored lines, and then gently cut, with a sawing motion, through the shortbread. Wipe the knife clean between cuts, and brush crumbs frequently from the cutting board to keep the shortbread neat and tidy.
23. So ahead: the shortbread dough can be made and frozen in the pan, unbaked, up to 2 months ahead. Baked/finished bars can be frozen, tightly wrapped, for up to 1 month. Let defrost at room temperature before cutting.