Place all of the Oreos in a food processor or high-power blender. Pulse to crush into fine chunks. If you don't have a machine, place the Oreos in a large ziplock bag and crush with a rolling pin or heavy object.
Once the Oreos are crushed, add the whole tub of cream cheese and vanilla extract. Pulse again until the mixture is smooth and thick. Use a rubber spatula to transfer the Oreo mixture to a bowl. Cover and place in the fridge for 30 minutes. This will make it easier to roll into truffles.
Once the mixture is chilled, roll into approximately 21 tablespoon-size balls. Use a small cookie scoop or melon baller for even sizes. Place the truffles on a parchment-lined plate or small baking sheet, and freeze for an additional 30 minutes.
Ideally, you want the chocolate shell to be tempered so that it has a nice snap when you bite into it. If you are familiar with tempering chocolate, use the method you are most comfortable with. This easy microwave tempering method was learned from Sugar Geek Show (see link in blog post).
Place the chopped chocolate in a plastic or silicone bowl and microwave for 30 seconds. Stir well with a spoon or rubber spatula. Microwave for another 30 seconds, then 15, then 10, then 10 seconds, stirring well in between each heating. The most important thing is that the chocolate does not go above 90ºF. Use a candy or probe thermometer to check the temperature of the middle of the melted chocolate. If it is ever too hot, keep stirring to incorporate air, and add a few pieces of un-melted chocolate to cool it down. If necessary, continue with 10 second intervals, stirring and checking the temperature, until smooth. If the chocolate is too thick, add a teaspoon of coconut oil. Use the back of your spoon or spatula to spread some melted chocolate on a piece of parchment paper. If it starts to solidify in a few minutes, then your chocolate is good to use.
Remove the truffles from the freezer and use 2 forks to gently coat them in chocolate, one at a time. Place a truffle in the bowl of chocolate, use the forks to roll it around, and lift the truffle, scraping the extra chocolate on the side of the bowl. Place on a parchment-lined baking sheet or plate. Repeat with all of the truffles. Use the extra chocolate to drizzle on top of the truffles.
Store in the fridge for at least 1 hour, transferring to an airtight container once the chocolate is fully set. Most people prefer to enjoy these truffles cold from the fridge! See below for storage instructions.