Combine your sugar and milk in a bowl, stir to combine until sugar has dissolved.
Crumble up your 10-12 oreos, you can use a food processor or crush with a rolling pin, in a bag, etc. until they are a fine powder or in small pieces.
Add your heavy whipping cream, vanilla and oreo pieces to the milk and sugar, combine in your stand mixer or with your hand mixer.
Put in the refrigerator and allow to chill for at least 4 hours, I would recommend overnight if at all possible. If you haven't already at this point, add your ice cream maker bowl to the freezer and allow to freeze. It has to be frozen before you start making your ice cream.
Add your ice cream base mixture to your frozen ice cream bowl and turn on your ice cream maker. Some models recommend starting the ice cream machine before you add the mixture, follow your ice cream maker's instructions.
Allow to spin for 30 minutes or so, (depending on your specific maker) and check on it periodically.
Remove from ice cream maker, top with additional oreo pieces if desired.
Store in an air-tight container in the freezer.