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For the cookies:
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Place the flour, cocoa, icing sugar, baking soda, cream of tartar and butter into your food processor with the blade attachment. If you're doing it by hand, place all of the ingredients in a large bowl and rub the butter into the flour until it resembles breadcrumbs. If using your food processor, pulse until the mixture resembles breadcrumbs, about 10 seconds.
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Place the egg and vanilla extract into a small glass and lightly beat. Pour over the dry ingredients. Pulse until well combined. At this stage, the dough will have bigger lumps, but still won't be quite together. So add in the milk, one tablespoon at a time until a soft dough forms.
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Turn the dough out onto a piece of plastic wrap and bring the edges of the plastic together. Wrap the dough up. Place the dough in the fridge for around 2 hours.
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After the dough has chilled, preheat the oven to 190 C (375 F) and line 2 baking trays with a Silpat mat or parchment paper.
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Lightly flour your work surface and turn the dough out. Roll the dough out until 1/4 inch thick. Cut your cookies out using your preferred cutter. I used a 2 and 1/2 inch heart cutter. You don't have to do hearts, you can do any shape you like! You may end up with more or less cookies depending on the size of your cutter. Re roll the scraps and repeat until you've used all the dough.
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Place your cut out cookies onto your baking trays. Once all the dough has been used, place the cookies in the oven for 12-15 minutes until firm to the touch and risen slightly. Then remove the trays from the oven. Leave cookies to cool on the baking trays for 5 minutes before transferring to a wire rack to cool completely.
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Once the cookies are cooled, make the frosting. Break the white chocolate up and place into a heatproof bowl. Add in the butter. Either place the bowl over a saucepan of simmering water or place in the microwave in 20 second bursts until fully melted.
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Sift the icing sugar into a medium sized bowl and then pour the melted chocolate and butter mixture over it. Beat until combined. You'll notice it doesn't quite beat together smoothly, so add the milk a tablespoon at a time until you have a spreadable filling. Using an angled spatula, spread frosting onto the bottom of 12 of the cookies and then place the remaining 12 cookies on top of the frosted cookies.
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Cookies will keep in an airtight container for up to 3 days.
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Recipe for cookies adapted from Rosie's Bakery All Butter, Cream-Filled, Sugar-Packed Baking Book. Recipe for the filling by me, Annie.
