Salted Dark Chocolate Caramel Stuffed Cookies

I get it. Courtney's Boston Cream Cupcakes looked awesome. I figured her recipe was so popular, I could share a slightly more-complicated-than-usual dessert recipe of my own. It even has a long title to prove to you that it's all fancy-shmancy (see previous post claiming recipes are not difficult: oops). The reason I turned to Sally for this one is because Will is an avid lover of caramel. I'm sure I've talked about it before, but I really can't explain how much the guy loves his caramel-flavored desserts. I can't even bring caramel squares into the house without him eating half of them before I actually use them in a recipe. It's convenient on occasion because I always know what flavor dessert to surprise him with or what indulgent coffee to pick out for him if I'm out running errands. A simple man with simple needs. So when I came across this cookie recipe on Sally's blog, I knew it was perfect. After how much he loved the caramel molasses cookies, I knew something that was salted, caramel and in cookie form, would be a hit.

I have to admit that even I, baking (sort-of) extraordinaire, was a bit turned-off by how many steps this recipe had, especially considering she says it only yields 15 cookies! A) Sally has to make the most giant cookies in existence because I always get at least one and a half times the cookies she does per recipe and b) seriously too much work for the result of a mere 15 cookies. Excuse me if I'm indignant and like my cookies to last more than a day, because at the rate Will and I inhale a good batch of cookies, 15 would barely make it a day in our house. But I wanted to put a smile on Will's face since he's been having a stressful semester due to a bunch of back-to-back snow days at the beginning of the term, which has led to a pile-up of projects and papers in all his classes at this point. So was I willing to put in all the effort for two dozen cookies to make him happy and give him something to be happy about? Sure thing. I even threw in dark chocolate chips to make these completed tailored to him. Give them a shot and don't be dissuaded by the longer recipe!

Baking Notes: I chose to use dark chocolate chips since that is what Will always prefers. I also ended up using regular baking caramels as opposed to Rolo's because I had enough hidden in my cupboard from the last caramel recipe.

Salted Dark Chocolate Caramel Stuffed Cookies (adapted from Sally's Baking Addiction; makes 2 dozen)
2 1/4 cups all-purpose flour, measured

1 tsp baking soda
1 1/2 tsp cornstarch
1/2 tsp salt
3/4 cup unsalted butter, melted
3/4 cup light brown sugar, loosely packed
1/2 cup sugar
1 large egg + 1 egg yolk
2 tsp vanilla bourbon extract
1 cup dark chocolate chips, divided
15-20 caramel candies, halved
Sea salt, for sprinkling

In a large bowl, mix the flour, baking soda, cornstarch and salt - set aside. In a medium bowl, whisk the melted butter, brown sugar and white sugar until no brown sugar lumps remain. Whisk in the egg, then the egg yolk, then the vanilla bourbon extract. Pour the bowl of wet ingredients into the dry ingredients and mix together gently with a rubber spatula, creating a soft dough. Fold in 1/2 cup chocolate chips - if they don't stick very well, that's okay. Just try to get them as mixed in as you can! Cover the dough and chill for at least two hours or up to three days.

Once the dough has been properly refrigerated, take it out of the fridge and allow it to slightly soften at room temperature for 10 minutes. Preheat the oven to 325 degrees and line two baking sheets with parchment paper or silicone baking mats, then set aside. Unwrap your caramel candies and cut them in half. Prep the other half of your chocolate chips in a pile.

Roll the dough into balls, about 1 1/2 tbsp to 2 tbsp each. The following process is what I did to make the caramel surprise snickerdoodles. Split the ball of dough in half, make an indention in one half of the it, stick your caramel in the middle, then place the other half back over it, rolling again to remake your dough ball. Once your dough ball is reshaped, flatten it just a smidge to press a few more chocolate chips onto the top. Once you've got a sheet of cookie dough balls, sprinkle fresh ground sea salt over the cookies sheet. Bake for 12-13 minutes - cookies will look underbaked and soft, but they will continue to bake once you remove them. Repeat the process until all dough is used up!Allow cookies to cool on the sheet for 10 minutes before removing to a wire rack to cool. Allow to cool another 10 minutes on the cookie rack, then enjoy!

Recipe: Sally's Baking Addiction: Salted Caramel Chocolate Chip Cookies