Step 1: Prepare the Shortbread Cookies: In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. Beat in the vanilla extract.
Step 2: In a separate bowl, whisk together the all-purpose flour and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined and a soft dough forms.
Step 3: Divide the dough in half, flatten each half into a disc, wrap in plastic wrap, and chill in the refrigerator for at least 30 minutes.
Step 4: Preheat oven to 350°F (175°C). Line baking sheets with parchment paper. On a lightly floured surface, roll out one disc of chilled dough to about ¼-inch thickness. Use a 2-inch round cookie cutter and a ½-inch round cutter (or a piping nozzle/bottle cap) to cut out donut shapes. Repeat with the second dough disc and any scraps.
Step 5: Place cookies on prepared baking sheets and bake for 10-12 minutes, or until the edges are lightly golden. Let cool completely on a wire rack.
Step 6: Prepare the Toasted Coconut: While cookies cool, spread the shredded coconut on a baking sheet. Toast in the preheated oven (or in a dry skillet over medium-low heat) for 8-10 minutes, stirring occasionally, until golden brown. Watch carefully to prevent burning. Set aside.
Step 7: Make the Caramel Topping: In a medium saucepan, combine granulated sugar, butter, milk, and heavy cream. Bring to a boil over medium heat, stirring constantly until the sugar dissolves. Reduce heat to low and simmer for 5-7 minutes, stirring occasionally, until the mixture thickens slightly and reaches a soft-ball stage (235-240°F / 112-115°C if using a candy thermometer). Remove from heat and stir in vanilla extract.
Step 8: Immediately stir the toasted coconut into the warm caramel until fully coated.
Step 9: Assemble the Cookies: Spoon about 1-2 teaspoons of the coconut caramel mixture onto each cooled shortbread cookie, spreading it evenly and creating a small mound on top of the cookie ring.
Step 10: Apply Chocolate Coating: Melt the chocolate using a double boiler or in the microwave in 30-second intervals, stirring until smooth. Dip the flat bottom of each cookie into the melted chocolate, wiping any excess. Place chocolate-side down on parchment paper. Allow chocolate to set (you can place them in the refrigerator for 10-15 minutes to speed this up).
Step 11: Once the bottom chocolate is set, drizzle the remaining melted chocolate over the top of each cookie in thin stripes. Let the chocolate set completely before serving.
Step 12: Enjoy your homemade Samoas!