Preheat the oven to 350°F degrees. Line two baking sheets with parchment; set aside.
In the bowl of a stand mixer, cream the softened butter and sugar together for about 2-3 minutes. It should be smooth and well combined.
Add the vanilla and milk. Mix until combined.
Add in the flour, baking powder, and salt. Mix until fully incorporated, scraping down the sides as needed.
Transfer the dough to a lightly floured work surface. Using a rolling pin, roll the dough into a rectangle about ¼ inch thick.
Using a round cookie cutter, cut out 2 ½ inch circles and place them onto a baking sheet. Then use a 1-inch cookie cutter to cut a smaller circle in the center of each of the larger round circles.
Transfer the cookies to the freezer for about 10 minutes.
Bake in the preheated oven for approximately 10 minutes, or until set. Do not overbake. Allow cookies to cool completely before assembly.
Make the topping
Spread the shredded coconut onto a baking sheet and toast in the preheated oven for about 10 minutes, stirring several times throughout the process to prevent burning. Watch closely. Remove from the oven and allow to cool.
Meanwhile, while the coconut is toasting, place the caramels and evaporated milk in a large pot. Heat over low heat and stir frequently for approximately 10 minutes. Caramel should be melted and smooth.
Using a spatula or knife, spread a layer of caramel over the top of each cooled cookie.
Add the toasted coconut to the remaining caramel. Stir until well combined.
Allow to cool slightly. Using gloved hands, place about a tablespoon worth of the coconut caramel on top of each cookie, shaping it to the cookie. As the caramel cools, it will harden. Work quickly to finish the remaining cookies.
Melt the chocolate and vegetable oil in the microwave in 30-second increments, whisking in between, until smooth.
Dip the bottoms of the cookies in the melted chocolate and place on a piece of parchment to set.
Transfer the rest of the melted chocolate to a piping bag. Drizzle the chocolate over the tops of the cookies.
Notes
Storage: Cookies should be stored in an airtight container for up to 3 days.