Heat oven to 350°F. Line two large sheet pans with parchment paper or silicone baking mats.
In a large bowl, add the coconut flakes, flour, vanilla, and salt. Add every bit of the sweetened condensed milk. Use a hand mixer and mix just until everything comes together. Stop as soon as it’s combined. Pop the mixture in the fridge for 10 minutes so it can thicken. Spray a 1-tablespoon cookie scoop with cooking spray, then scoop firmly, packing the mixture into the scoop so each cookie holds its shape (see note 3).
Arrange on prepared pans, spaced 1 inch apart. Bake 10–14 minutes or until the tops are lightly toasted and the bottoms are pale golden. Watch closely; they can brown quickly. Remove from oven and cool on the pan for 5 minutes, then transfer to a cooling rack.
Optional: Once the cookies are fully cooled, melt the chocolate chips with the oil in a microwave-safe bowl. Microwave in 20-second bursts, stirring for 30 seconds between each burst to prevent overheating. Repeat until smooth and fully melted. Transfer about 1/4 cup of the melted chocolate to a small plastic bag and set aside.
Dip the base of each cookie in the remaining melted chocolate and place on parchment. Snip a tiny corner off the plastic bag and drizzle chocolate over the tops. Let chocolate set at room temperature.
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Notes
Note 1: These macaroons turn out best with soft, super fresh sweetened coconut. Feel the bags at the store and choose the softest one.Note 2: Any chocolate works. Milk chocolate is sweetest; semi-sweet or dark for less sweet cookies.Note 3: The mixture is sticky. Spray your scoop with cooking spray or help release the dough. Leave them rustic or roll balls gently by hand for a neater shape.Storage: Store tightly covered at room temperature for up to 3 days or in the fridge for 5–7 days (best within 1–2 days). To freeze (without chocolate): Freeze baked cookies on a sheet pan until solid. Transfer to an airtight freezer bag or container and freeze up to 2 months. Thaw at room temperature.