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1
Position racks in the lower and upper third of the oven and preheat to 325 degrees F. Line 3 baking sheets with parchment or silicone mats.
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2
(If you don't have 3 pans, simply cool the pan between batches.)
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3
Put the butter and the unsweetened and semisweet chocolates in a medium microwave-safe bowl.
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4
Heat at 75 percent power in the microwave until soft, about 2 minutes.
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5
Stir and heat again until melted, up to 2 minutes more.
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6
(Alternatively, put the chocolates and butter in a heatproof bowl.
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7
Bring a saucepan filled with an inch or so of water to a very slow simmer; set the bowl over, but not touching the water, and stir occasionally until melted and smooth.)
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8
Stir the light brown and granulated sugars and vanilla into the chocolate mixture with a wooden spoon.
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9
Add the eggs and buttermilk and beat vigorously until thick and glossy.
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10
In another bowl, whisk the flour, cocoa, cinnamon and salt together.
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11
Add the dry ingredients to the wet and stir until just mixed.
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12
Stir in chocolate chunks and dried cherries, if using.
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13
Drop the batter in heaping tablespoons onto baking sheets--a small ice cream scoop is ideal for this.
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14
Space the cookies about 2-inches apart.
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15
Bake until the cookies set but are soft and fudgy on the inside, 12 to 15 minutes.
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16
Cool cookies on the baking sheet for 5 minutes, then transfer to a rack to cool completely.
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17
Serve.
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18
Store cookies in a tightly sealed container at room temperature for up to a week.
