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Wilder Recipes: Kalamata Olive Shortbread Cookies

By Thewilderthings @TheWilderThings
Wilder Recipes: Kalamata Olive Shortbread CookiesWilder Recipes: Kalamata Olive Shortbread Cookies
Last week, my wonderful and brilliant boss did something wonderful and brilliant and arguably disastrous to my waistline. She brought in a package. "Someone gave these to me," she said. "And I was cleaning out my pantry and realized that somebody better eat them. So here, eat them." She put them on the filing cabinet next to my (standing, I might add) desk.
They were olive shortbreads, she said. I made a face. "Are they crackers?" I asked. "Are they cookies? Have they not made up their mind?" My coworker chimed in, mouth full of savory, buttery goodness. "Charlotte, just eat one. They are insane. They will blow your mind." I took a bite of a cracker-or-cookie and blacked from their savory, slightly sweet, rich, crumbliness and I can't remember the rest of my day (more after the jump).
I'm kidding; I only blacked out for an hour, not the whole day. No, in all seriousness, these cookies (crackers? The world may never know) changed the way I think about shortbread. I'm accustomed to shortbread that is usually about half-an-inch thick, sweet, sprinkled with granulated sugar, and magically shows in tins in my apartment around Christmas. I've never bought or made the stuff in my life—it just appears and I eat it without giving any thought to its provenance. 
But these? I wanted to learn how to make. After some Googling, my coworker came across this recipe from Heidi Swanson's famous and wonderful blog 101 Cookbooks. It was simple: butter, flour, powdered sugar, a bit of salt, olive oil, and (of course) Kalamata olives. Real shortbread...with olives.
Heidi's recipe calls for chilling the dough in the refrigerator after you've rolled it out (between two pieces of parchment paper, but I used waxed and it was fine) for at least 45 minutes. I was impatient and found that putting it in the freezer for 20 worked just as well. Work quickly when cutting out the dough, because as it warms up the butter starts to melt and the rounds become hard to transfer to the baking sheet. Heidi says to bake the cookies on parchment paper, but I didn't have any, so I just put a thin layer of olive oil on the baking sheet and they released easily. She also says to bake the cookies for at least 12 minutes if they're tiny; mine ended up being about a 1/3-inch thick and the cutter I used was about 2 inches in diameter. So I baked them at 350 degrees for 8 minutes, then rotated the baking sheet and baked them for 8 minutes more. They came out perfectly. The yield was about 35 cookies.
Wilder Recipes: Kalamata Olive Shortbread Cookies
I liked the fluted edge of the cutter I used, it made the cookies look a little fancier. I think these would probably be really good with some finely chopped hazelnuts sprinkled throughout. That's my next move. For now, I'm going to bring this batch to work and plunk them down next to my boss (and far, far away from me).
INGREDIENTS:
9 tablespoons unsalted butter, room temperature
3/4 cup powdered sugar, sifted
1 tablespoon extra-virgin olive oil
1 1/4 cups all-purpose flour
1/2 cup cured olives, pitted and chopped
two pinches of sea salt
INSTRUCTIONS:
Using a wooden spoon, stir the butter in a large bowl until it's creamy and light. Add the sugar, stir until it's well-mixed, then add the olive oil, stirring until combined. Stir in the flour by hand in batches; when it's fully incorporated, add the olives and salt and stir just until the olives are evenly distributed throughout the dough. Heidi says you'll end up with a sticky dough, but mine was a bit more crumbly and I had to kind of shove it together (yes, that's a technical kitchen term) to get it to stick to itself.
Place the dough in the middle of a large piece of parchment or wax paper, then cover it with a second piece of parchment paper and roll out the dough until it's 1/4-inch thick. The dough is sticky and somewhat melty, so the paper makes it possible to roll and saves you from having to scrub the roller. Refrigerate the dough for at least 45 minutes or overnight, or you can do what I did and stick it in the freezer for 20 minutes.
Preheat the oven to 350F with racks in the top and bottom third. Line two baking sheets with parchment paper or coat them with a thin layer of olive oil; I poured about a 1/2 tablespoon on and then used a paper towel to distribute it. Stamp out the cookies using whatever size sharp-edged cookie cutter you want. Sharp edges are essential for cutting through the olives; a glass won't work. Bake until the edges of the cookies are golden, rotating the pans from top to bottom, front to back once after about 8 minutes. Bake for about 12 minutes total for small cookies, and about 16 minutes for larger ones. But basically, just keep watching them, as the edges turning golden-brown will tell you when they're done baking.
Take them out and let them cool, then try not to eat them all in one sitting. 
Wilder Recipes: Kalamata Olive Shortbread Cookies

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