Dessert: Cinnamon Roll Cookies

This is a meandering musing about Christmas cookies. It’s kind of two unrelated stories that I’ve joined together, but it’s what popped into my head when I started thinking about what to say about the cookies I made.

I was having a conversation with a friend about Christmas cookies a week or so before Christmas, and we got to talking about the deterioration of quality of baked goods as people age. I won’t lie—it was a pretty mean conversation, in some ways. She was complaining about her mother’s poor execution of the sausage balls over Thanksgiving (Bisquick, bulk sausage, and cheddar cheese, the recipe is here, if you want it; in the manner of so many things that are made with what I call “low rent” ingredients, they are embarrassingly tasty), and I was telling her about Alex’s grandmother’s Christmas cookies.

I was assured that at one time, Grammy’s cookies were second to none. I’m not sure if that was an opinion clouded by the passage of time, or biased by affection, or possibly both, or if Grammy’s cookies had really once been great and had just gotten awful. But trust me, they were horrible. The only ones I can actually remember her making are Mexican wedding cakes. I think the truth was that she made several things—chocolate chip, fruitcake cookies and some fudge as well as other things, but they all seemed to be little stones covered with powdered sugar (they were all little stones, but I think the fact that they were all covered in powdered sugar had to do with them all being in the tin together and the sugar sifting off of the wedding cakes and on to every other thing around them). We always thanked her profusely and assured her we’d eat them on the way home.

Of course we never told her how they really were, nor what we really did with them (I can be mean, but I’m not that mean), which was to sow them along the roadside between Adams, MA and Falls Church, VA at regular intervals. Every so often we’d declare it to be time for a cookie, choose one, and announce the type. Only what we’d say was something like, “Mexican wedding anvil!” or “Chocolate chip brick!” or similar, and hurl it out the window. Then we’d say something witty like, “Oops! Sorry about that, Mr. Squirrel! I’m sure the swelling will go down in a couple of days!” or “Uh oh—that Jersey wall will never be the same again!” And you’re wondering why CBS still has Letterman in its late night line up instead of us.

And then when I started making my own Christmas cookies this year, I realized I’m bored with the same old Christmas cookies we’ve made every year. Chocolate chip. Oatmeal raisin. Peanut butter. “Magic” cookies (which aren’t “magic” cookies in the Eagle Sweetened Condensed Milk recipe definition, and in fact are actually a recipe called Favorite Chocolate Caramel Nut Bars and came out of a package of Kraft Caramels in the 1980s, but for some reason my grandmother always called them magic cookies, so that’s what I call them, but it always confuses people, who think they’re the kind made with a can of sweetened condensed milk, shredded coconut, and chocolate chips, and my high school English teacher just had an aneurism because this whole parenthetical aside is textbook case of comma abuse). Toffee Nut Bars. Brownies. I guess I’m just jaded, but all of those things just sound boring, boring, boring.

So I decided to come up with something a little different, and all my own. I got to thinking about things I’d like to translate into cookie form, and for some reason I thought of cinnamon rolls. At first I thought about doing them as an actual roll, but that experiment wasn’t much of a success. The dough I chose is pretty easy to work with, but doesn’t lend itself to being rolled out, filled, and rolled back up. It would make an admirable refrigerator log cookie (in fact, that’s its true application), but as a rolled up filled deal, not so much. So I decided to make them a thumbprint cookie, something I’ve had trouble with in the past, but figured I’d give another try.

I won’t keep you in suspense--they did work. My husband even liked them (he’s my harshest critic when I’m developing my own recipes, and he usually curls his lip at about 1/3 of everything and sends me back to the drawing board. With, I should hasten to add, constructive feedback for improvement). I got feedback from some other tasters, primarily about the distribution of filling within the cookie, which I’ve included within the recipe instructions.

The cookie part of these isn’t particularly sweet, which is good because the filling would make your teeth ache if you ate it on its own, and they both have a sort of crumbly tenderness to them. So they balance and complement each other pretty nicely. The topping could be piped on or spread on with a spoon, or if you prefer to drizzle for aesthetic purposes, you could—just add a bit more heavy cream until the icing is thin enough.

It’s possible that in another 40 years, my children or grandchildren will toss these out a car window yelling, “Cinnamon Roll rock!” but as long as they thank me profusely when I give them the cookies, I’ll be none the wiser.

Cinnamon Roll Cookies

makes 24-30 cookies

Ingredients

Cookie dough
2 sticks butter, softened
½ cup + 1 Tablespoon granulated sugar
2 ½ cups all purpose flour
1 teaspoon vanilla extract
1 teaspoon ground cinnamon
½ teaspoon kosher salt

Pecan Sugar Filling
½ cup pecans
½ teaspoon cinnamon
¼ cup light or dark brown sugar
1 teaspoon water

Icing
2 ½ ounces cream cheese at room temperature
3 Tablespoons powdered sugar
1 teaspoon lemon juice
2-3 teaspoons heavy cream (enough to make a
spreadable or pipable paste)

1. Preheat oven to 350 degrees
2. In a large bowl cream together butter and sugar.
3. When butter is light and fluffy, and sugar is fully incorporated, add the vanilla, salt, and cinnamon. Beat to combine.
4. Add flour slowly, mixing until just combined.
5. Form dough into 1” balls and place on a baking sheet covered with parchment paper.
6. In a food processor, combine pecans, sugar and cinnamon, and process until pecans are finely ground. With the motor running, add the teaspoon of water and pulse 8-10 more times until the mixture forms a thick paste.
7. Using your thumb, make a depression in each cookie. You can spread them out a bit
and make a fairly wide, shallow indentation, or make a deeper, more narrow indentation (the feedback I got was that the taster would have preferred the wide shallow configuration, because then they would have gotten a bit of filling in each bite; it’s a personal preference). These cookies don’t spread much as they cook.
8. Using a spoon or your fingers, fill each indentation with about a teaspoon of the pecan/sugar paste.
9. Bake 17-22 minutes, or until cookies are light golden and filling is set. Allow to set up for 5 minutes on the baking sheet, then transfer to racks to cool completely.
10. While the cookies bake and cool, make the frosting. Combine cream cheese, lemon juice and sugar in a small bowl and mix to combine. Pour cream in ½ to 1 teaspoon at a time, beating after each addition, until the mixture reaches a consistency you can either pipe or spread on the cookies (it should be a bit thinner than toothpaste).
11. Once the cookies have cooled completely, top each cookie with a dollop of icing (the icing can be piped using a pastry bag, a plastic bag with the corner snipped off, or you can just use a spoon to spread it gently over the filling).