Preheat your oven to 350 degrees F and pour the shredded coconut onto a baking sheet. Bake for 10 minutes, tossing halfway through, or until the coconut is lightly golden brown.
In a large mixing bowl, combine the toasted coconut, sweetened condensed milk, and dulce de leche, then set aside.
Add the Nilla Wafers into the bowl of your food processor, then pulse the cookies into small crumbs. Pour the cookie crumbs into the coconut mixture and stir until well combined.
Line baking sheets with parchment paper or a silicone baking mat, then scoop 1 tbsp rounds of the caramel coconut mixture onto the prepared baking sheets and repeat until all mixture is used.
Transfer the scooped truffles into the freezer for about 30 minutes to firm up.
In a microwave safe bowl, combine semi-sweet chocolate chips with vegetable oil. Microwave in 30 second intervals, stirring in between, until melted and smooth.
Dip the bottoms of each truffle into the melted chocolate and return to the prepared baking sheet.
Transfer the remaining chocolate into a ziploc bag, cut off one end, and drizzle it over the truffles.
Place in the fridge or freezer for 30 minutes to set the chocolate. Once set, carefully break off the excess candy-coating pieces around each truffle before enjoying!