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1
In the bowl of a stand mixer fitted with the paddle attachment, cream together the butter and sugar until light and fluffy.
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2
In a separate bowl, whisk together the flour, baking powder, and salt.
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3
In 3 increments, add the flour mixture to the creamed butter, mixing between each addition and scraping the sides of the bowl as necessary.
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4
Add the milk and vanilla extract, blending until combined and the dough begins to come together in large pieces.
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5
Use your hands to divide the dough in half and makes disc like shapes with each one.
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6
Wrap them each in plastic wrap and refrigerate until firm, about 1 hour.
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7
Once the dough has chilled, roll each disk out onto a lightly floured surface until it is about 1/8 inch thick.
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8
Cut out as many cookies as possible with a donut shaped cookie cutter.
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9
Place the cut out cookies on a Silpat or parchment paper lined baking sheet.
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10
Repeat with remaining dough.
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11
Bake the cookies for about 10-12 minutes, rotating the baking sheet halfway through, until the cookies are a pale golden brown.
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12
Immediately transfer to a wire rack and cool completely.
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13
Spread coconut flakes on a baking sheet lined with parchment paper.
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14
Bake the coconut for about 10 minutes in a 350F oven until toasted, stirring frequently to ensure even browning and so that it does not burn.
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15
Remove from oven and set it aside.
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16
Melt the caramels, milk, and salt on low on the stove.
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17
Cook, stirring until the caramels are fully melted.
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18
Remove from heat and combine 3/4 of the caramel mixture with the toasted caramel in a large bowl.
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19
Carefully spread the remaining 1/4 cup of caramel atop the cooled cookies then press on a portion of the coconut/caramel mixture.
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20
Repeat for each cookie.
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21
If the coconut/caramel mixture becomes too hard to manage, reheat mixture on very low heat until spreadable again.
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22
Melt the dark chocolate in microwave on on stove on low.
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23
Once fully melted, dip the bottoms of the cookies in the chocolate and place them on wax paper.
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24
Drizzle some chocolate over the tops of the cookies as well.
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25
Let the cookies sit until chocolate fully hardens.
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26
Helpful tips!
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27
*No donut shaped cookie cutter?
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28
Use a regular cookie cutter and a small dry spice lid for the smaller hole.
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29
*If dough is too firm after being in the fridge, let it rest at room temp for 10 min.
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30
*The shortbread should be very pale in color.
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31
When in doubt, underbake it!
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32
*Coconut burns very quickly so keep an eye on it and stir often!
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33
*Spreading the cookies with the reserved 1/4 cup of caramel gives the coconut mixture a sticky base to adhere to.
