Holiday Sandwich Cookies

Cait and I seem to have developed a tradition in recent years of getting together and baking something in time for the holidays. Usually there’s much yelling (both at each other and at what we’re doing) and definitely too much giggling. Last year we made biscotti, and the year before that we came up with those rum balls that got us wasted. This year I got to pick, and, as I’ve been craving Oreos recently, I went with that for inspiration and found this recipe from Chatelaine.

It started with us making a trip to Dollarama for some unrelated items, and Cait managed to find a three-pack of teeny tiny Santa hat hair clips. Note our manic expressions. I’m surprised mine actually stayed in my hair the whole night.

It did not stay in Gren’s hair. He was not a fan.

Start with your dough, because you’ll need to refrigerate it for a bit. In a bowl, whisk together 1 1/2 cups all purpose flour, 1 cup unsweetened cocoa powder, and 1 1/2 teaspoons baking powder (I doubled the recipe because there were two of us).

Then, in the bowl of your mixer, plop 1 cup room temperature butter and beat it with 1 cup granulated sugar until it’s fluffy and lovely.

Then drip in 1 teaspoon vanilla and 1 egg and beat that until fluffy.

Slowly, using a shield, add the flour mixture to the butter mixture and beat until well combined. The dough will be very stiff.

Separate that into two sections, flatten them into discs, and chuck them in the fridge for at least an hour. I made ours into little logs, which we then labeled “poos” for the rest of the night. We are very mature.

Now you can make your filling. Beat up 1/2 cup room temperature butter until soft and creamy, then add in 2 1/2 cups sifted icing sugar (slowly) and beat until combined. Drizzle in 2 tablespoons (or more) whipping cream until you have a nice thick fluffy icing. Then you add in 1/4 cup crushed hard candy.

Now, Cait made hers with crushed candy canes (the recipe calls for peppermint candies but they’re pretty much the same).

I, however, have a strong aversion to candy canes. So I used Werther’s hard candies instead.

Here is Cait smashing up some Werther’s for me.

So we split the icing into two parts and mixed the candy canes into one half and the hard caramels into the other.

Now, when your dough is chilled enough, preheat your oven to 375°F and spray several baking sheets or line them with parchment (which is what I did). Grab one of your chilled discs of dough and roll it out on a floured surface (or between two sheets of waxed paper, which is what I’m doing here). Dust things with flour if they get sticky.

Use cookie cutters to get some good sandwichy shapes. Cait was in charge of this as I rolled out the dough. She was very careful to make sure she made at least two of everything, for sandwichy purposes.

Gather up your scraps and chuck them back in the fridge to re-roll after ten minutes or so. Make sure to use all the dough! Place the cut cookies on your baking sheet and bake for 8 minutes, rotating the sheet halfway through. The cookies will expand somewhat so don’t put them too close together.

Set the baked cookies on a wire rack to cool completely.

Cait made this cookie corgi specially for the Pie.

Now sit down with your cooled cookies and your frosting and a small knife and start pasting icing onto one side of a cookie. We watched Elf as we did this, to get into the holiday spirit.

Match it up and squish it down (not too hard – they will break if you press them too hard).

And that’s it. Sandwiches! They’re supposedly best eaten the day they’re made but I actually preferred them the next day when they were a little chewier. But that’s up to you.

Store whatever you can’t eat in an airtight container.