The Chocolate Sandwich Cookies I Beg My Sister to Bake Every Year

My favorite gift from my younger sister is cookies. Chocolate sandwich cookies to be exact. When we were in high school, she uncovered—and perfected—a recipe for homemade Oreos. I can picture her in the kitchen, earnestly focused on filling each cookie with a generous dollop of buttercream. I'd beg her to make them when we were home together.

Ever since then, she'll occasionally surprise me with a package of them in the mail. When I see a box outside my door with her return address in Maine, I hold my breath hoping it's cookies. I unpack them and store them in the freezer. I savor each one, eating them in tiny bites to make them last. I love how good they taste: the rich chocolate wafers, the sweet filling with a touch of vanilla and salt to balance the sugar. I love that the cookies are crisp on the edges and slightly soft in the center so they don't shatter too much under your teeth. And, most of all, I love that they're a labor of love.

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There are so many homemade goodies that make excellent gifts. You can make your own caramels, wrap up miniature pound cakes, or pack a jar with your own cocktail cherries. But I believe there's something especially alluring about homemade sandwich cookies, and not just because of my sister. (Although that helps!)

The nostalgia of faux Oreos appeals to just about everyone, and with this recipe, you can customize them with fun fillings. I can't imagine anything more whimsical for the holidays.

I've tried all manner of fillings from birthday cake (flavored with imitation vanilla and sprinkles) to dark chocolate espresso. But my top three favorites are whipped tahini (like a more sophisticated cousin of a peanut butter filling), peppermint (because what's better for the holidays?), and matcha white chocolate (a wildly green creation that will win over every kid on your list).

Start with the base recipe for the cookies. Be sure to let them cool fully, then fill with your favorite frosting or filling.

Chocolate Sandwich Cookies

View Recipe

Ingredients

1/2	cup (113 grams, 1 stick) unsalted butter
1	tablespoon vegetable oil
2/3	cup (132 grams) granulated sugar
1	teaspoon vanilla extract
1/2	teaspoon salt
1	egg
1/4	cup cornstarch
1/4	cup black cocoa powder (you can use all regular cocoa if you prefer; this will just give a more intense color)
1/4	cup Dutch-process cocoa powder
1/2	teaspoon espresso powder
1 1/2	cups (180 grams) all-purpose flour

1/2	cup (113 grams, 1 stick) unsalted butter
1	tablespoon vegetable oil
2/3	cup (132 grams) granulated sugar
1	teaspoon vanilla extract
1/2	teaspoon salt
1	egg

1/4	cup cornstarch
1/4	cup black cocoa powder (you can use all regular cocoa if you prefer; this will just give a more intense color)
1/4	cup Dutch-process cocoa powder
1/2	teaspoon espresso powder
1 1/2	cups (180 grams) all-purpose flour

Matcha White Chocolate Sandwich Cookie Filling

Peppermint Sandwich Cookie Filling

Whipped Tahini Sandwich Cookie Filling

What's your favorite holiday cookie? Share recipes in the comments section below!