Step 1: Prepare the Cookie Dough

1. Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper.
2. In a large mixing bowl, combine the flour, sugar, and salt.
3. Add the cold, cubed butter and mix using your hands or a pastry cutter until the mixture resembles coarse crumbs.
4. Pour in the milk and vanilla extract, then mix until the dough comes together into a ball.

Step 2: Roll and Cut the Dough

1. Lightly flour a clean surface and roll the dough to ¼-inch thickness.
2. Use a round cookie cutter to cut out circles, then use a smaller cutter to make holes in the center, giving the cookies their classic donut shape.
3. Transfer the cookies to the prepared baking sheet.

Step 3: Bake the Cookies

1. Bake the cookies for 10-12 minutes or until the edges are golden brown.
2. Let the cookies cool completely on a wire rack.

Step 4: Prepare the Caramel-Coconut Topping

1. In a saucepan, melt the caramel candies with the heavy cream over low heat, stirring constantly until smooth.
2. Stir in the toasted shredded coconut until well combined.
3. Remove the mixture from the heat and let it cool slightly for easy handling.

Step 5: Assemble the Cookies

1. Spoon the caramel-coconut mixture onto the top of each cookie, spreading it evenly and pressing gently to adhere.
2. Allow the topping to set for about 10 minutes.

Step 6: Add the Chocolate Coating

1. Melt the semi-sweet chocolate chips with the coconut oil in a microwave-safe bowl, heating in 20-second intervals and stirring until smooth.
2. Dip the bottom of each cookie into the melted chocolate and place it back on the parchment-lined baking sheet.
3. Drizzle additional melted chocolate over the top of each cookie using a spoon or piping bag.

Step 7: Let the Cookies Set

1. Let the cookies sit at room temperature until the chocolate hardens, or refrigerate them for faster setting.
2. Once fully set, serve your homemade Samoa Cookies and enjoy!