Crush 6 cookies in a plastic bag with a rolling pan. Leave some larger pieces for texture. Set aside.
Twist off the top cookie of the remaining 8 sandwich cookies and place a popsicle stick in the middle of the cream. Place the top cookie back on top so you have a cookie “pop.”.
Whisk together coconut milk, sugar and vanilla extract, sweetening to taste.
Add your cookie pops to your popsicle mold. Pour the milk mixture in and cover the sandwich cookie at the bottom of the mold. Alternate between adding cookie pieces and coconut milk 2 to 3 more times, until the molds are filled.
Place the lid on the mold and transfer to the freezer for 4 hours, or until frozen.