Cream together butter and sugar in a large bowl. Mix in flour, baking powder and salt at a low speed. Next, add the vanilla and milk, adding in the milk only as needed to make the dough come together without being sticky (you may not need any at all). The dough should come together into a soft, pliable ball. Add in a bit of extra flour if your dough seems sticky.
1 cup butter, 4 ounces granulated sugar, 9.8 ounces all purpose flour, 1/4 teaspoon baking powder, 1/2 teaspoon salt, 1/2 teaspoon vanilla extract, up to 2 Tablespoons milk
It's easiest to roll the dough out in 2 or 3 batches (between pieces of wax (or parchment) paper to about 1/4-inch thickness (or a little thinner). You can optionally chill the dough for an hour or up to overnight if needed.
Use a 2 inch cookie cutter to make the rounds. Place on a parchment lined (or on silicone mat) baking sheet and make a hole in the center. I used the small end of a large round piping tip (#12) to make the small hole. Repeat until the dough is used up (it's okay to re-roll, this dough is shortbread-like and very forgiving.) I used the small end of a large round piping tip (Wilton #12). Repeat until the dough is used up (it's okay to re-roll, this dough is shortbread-like and very forgiving.)
Bake cookies for 10-12 minutes, until bottoms are very lightly golden brown around the edges.
Cool for a few minutes on the baking sheet, to allow them to firm up slightly, then transfer to a wire rack to cool completely.
Preheat oven to 300F.
Spread coconut evenly on a rimmed baking sheet and toast 20 minutes, stirring every 5 minutes, until coconut is golden. Watch carefully, especially near the end of toasting time; the coconut toasts very quickly once it begins to become golden.
8.3 ounces shredded coconut
Cool on baking sheet, stirring occasionally. Set aside.
To Make the Topping
Unwrap the caramels and place in a large microwave-safe bowl with milk and salt. Cook on high for 3-4 minutes, stopping to stir a few times to help the caramel melt. When smooth, fold in toasted coconut with a spatula.
Using the spatula or a small offset spatula, spread topping on cooled cookies, using about 2-3 teaspoons per cookie. Reheat caramel for a few seconds in the microwave if it begins to firm up, to make it soft and spreadable once again.TIP - To make it a little easier to spread the topping on, you can first smear some reserved caramel on top of the cookies. Then, add the caramel-coconut topping using clean fingers. Wet your fingers with water to help prevent the mixture from sticking.
While topping sets up, melt chocolate in a small bowl. Heat on high in the microwave in 45 second intervals, stirring thoroughly to prevent scorching. (I melted mine stovetop using double boiler method.)
8 ounces dark or semisweet chocolate
Dip the base of each cookie into the chocolate and place on a clean piece of parchment paper. Transfer all remaining chocolate into a piping bag or a ziplock bag with the corner snipped off and drizzle finished cookies with chocolate. (Melt a bit of additional chocolate, if there is not quite enough for each cookie.)
Let chocolate set completely before storing in an airtight container.
Be sure to weigh your flour with a kitchen scale for the best results. Too much flour can make shortbread crumbly and dry, which happens often when you overmeasure finicky flour. Pull out your butter and let it sit at room temperature 30 minutes to an hour before you begin.
You can use either sweetened or unsweetened coconut, though I prefer to use unsweetened as the caramel it's mixed with is sugary enough.
For the caramel, the store bought wrapped caramels work really well. Kraft, Werthers, and Brach's are all great options, so long as you grab the chewy caramels and not hard candy. Even the Kraft caramel bits will work!
Semi-sweet or even dark chocolate chips are preferable for homemade Samoas. Milk chocolate would work, though the cookies might be a tad too sweet. It all depends on preference.