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I have just packed up 12 dozen cookies for my annual cookie exchange. And since every bag is topped up with a couple extra, it’s actually more. So I just baked approximately 200 cookies.

Ahhh. Let me just pause here a minute, and take a sip of my well-deserved glass of wine.

Except I didn’t bake 200 cookies. This year, I got it in my crazy head that I wanted to make sandwich cookies. So really, I baked 400. But let me back up a second.

Tomorrow is my friend Susan’s annual cookie party, wherein a dozen or so friends get together for snacks, wine, catching up, and supplying one another with a festive season’s worth of baked goods. We each bake up huge batches of one cookie, divvy them up among us, and then go home with a bunch of different kinds of cookie. You can bring them to family gatherings, pack up a fancy selection to give as gifts, and you can have a stockpile of cookies in the freezer for when a sugar craving takes you. It’s genius!

It’s the kind of community-building thing I love to be a part of. It ensures that I see these friends at least once a year, and it reminds me that many people working together can achieve greater things than we can do on our own. I also love the baking.  My mom did cookie exchanges when I was a kid, and a lot of my Christmas memories are tied up in those weekend afternoons spent with her rolling out cookies by the hundreds, watching snow collect in the pine trees outside the kitchen window.

As a tradition, the cookie exchange is a pretty worthy one to establish and nurture, but there are a couple of key elements to making it work.

1. Involve only friends who like to bake, and are excellent cooks. You want people who will enjoy the work, and who will make cookies that you want to eat.

2. Kids can help, but they don’t get creative control. Meaning: nothing with mismatched sprinkles, neon icing or botched/unrecognizable cutout shapes. This may sound fairly hardline, but seriously, I put a lot of thought and care into the cookies I make every year and hope for some nice grownup cookies in return.

3. The cookies should be delicious, but not labour-intensive. Case in point, icebox cookies. You shape the dough into a log, chill it, and just slice and bake. And as long as the cookie is super delicious – such as the tart and shortbready Lime Meltaways – you’re still giving people something really nice.

This year, in deciding what cookie to make, I found myself daydreaming about a chocolate-mint combination. I wanted something that would approximate the After Eight mint in cookie form. This meant a sandwich cookie, but decided that I could justify the extra work as long as I stayed with the icebox cookie format.

It took me a while to find the right recipe. I tried the chocolate variation of Smitten Kitchen’s icebox cookies, but I couldn’t get it chocolatey enough. Plus, it was too shortbready and crumbly to support a filling. I ended up tweaking a recipe from the hilariously retro Betty Crocker Cooky Book, which yielded a nice solid, crispy cookie. I bumped up the flavour with both melted chocolate and cocoa, plus a hefty dose of peppermint extract. For the filling, I took my guidance from the cream cheese mints of my youth, only used less icing sugar.

Combined, the dark chocolate cookie and the rich minty icing are a cookie I’m quite proud of. Not quite an After Eight mint in cookie form, but pretty close.

After Eight Cookies
makes about 8 dozen filled cookies

Cookie dough:
2 3/4 cups all-purpose flour
1/2 cup cocoa
1/2 tsp. baking soda
1 tsp. salt
1 cup softened butter
1 cup white sugar
2 oz. bittersweet chocolate, melted and cooled slightly
2 eggs, room temperature
1 1/2 tsp. vanilla
2 tsp. peppermint extract

Icing:
4 oz. cream cheese (This is half a rectangular package of Philly; I use full-fat.)
2 cups sifted icing sugar
1 tsp. peppermint extract

1. Sift together the dry ingredients and set aside. In a stand mixer (or mixing by hand), cream the butter and sugar together until the mixture is well-incorporated, fluffy and creamy. Add the vanilla, peppermint and melted chocolate, and mix completely, scraping down the sides of the bowl. Add eggs one at a time, scraping down the sides of the bowl to ensure the egg is evenly distributed (but don’t beat so much that it’s completely incorporated). Add the dry ingredients in three instalments, scraping down the sides of the bowl each time.  Remove the dough from the mixing bowl, wrap in plastic wrap, and chill it for about 1/2 hour in the fridge.

2. Divide the dough into four equal pieces, and roll each into a log about one and a half inches in diameter. Wrap each log in plastic wrap and chill in the fridge for at least two hours.

Tip!  Want to ensure that your cookies will be nice and round? Keep a few paper towel cardboard rolls on hand, and slip the dough inside these to chill. They help the dough keep its shape as it chills.

3. Preheat the oven to 400 degrees Fahrenheit. Cut the dough into 1/8″ slices and arrange on baking sheets lined with parchment paper. Bake 5 to 8 minutes, removing from the oven when the bottoms are just slightly browned. Cool completely on a wire rack.

4. To make the icing, mix the cream cheese in a stand mixer (or a bowl, by hand) until fluffy. Add the peppermint extract, then the icing sugar in three installments, scraping down the sides of the bowl. This can be made ahead of time, and keeps well in the fridge for a couple of days.

5. When the cookies are completely cool,  sandwich them in pairs with a generous dab of icing. 

These cookies can be kept frozen but will keep well for a few days at room temperature.

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