Make cashew cream by first soaking the cashews in water at least two hours or overnight in refrigerator.
Next day, rinse them, and put them in blender. Add 1 cup of plant milk and blend until creamy. If you want it to be creamier and easier to pour into molds, feel free to add more of the plant milk at this point but hold some back for the next steps. Add in the maple syrup if you think it needs sweetening.
Remove half the cashew cream mixture and set aside - it's the vanilla portion of the popsicle mixture.
Add the black cocoa to the remaining cashew cream in the blender. Blend until creamy. Here is where you may need to add some or all of the remaining milk. This is your chocolate portion of the popsicle mixture.
Fill the popsicle molds by alternating between pouring the chocolate cream, adding oreo chunks, pouring the vanilla mix. I suggest pouring in a bit of chocolate cashew mix first before adding cookies. I added a cookie chunk at the tip of mine, and that made the tip break off of some of my pops, so next time I will first pour in the mixture and then start cookie-stuffing.
Do not chill the full fat cans of milk. Shake the room-temperature can to distribute the solids andn liquids inside. Pour the amount you need into a bowl.NOTE: You need about 1 cup per 4 popsicles using my mold so reduce the recipe if you want to make fewer popsicles.
Crush 5 oreos and add them to the coconut milk.
Add the vanilla and maple syrup and stir the mixture.
Add a whole oreo to each popsicle well. Pour in the mixture so the well is full.
Freeze the Popsicles (either method)
Freeze your mold for 30 minutes, then insert sticks.
Freeze your pops at least four hours or overnight.
To remove, dip mold in a pot of hot water and tug until they slide out. It's quite a process, don't let anyone tell you removing is easy. BUT once they are out, eat!