Place the chocolate sandwich cookies in a resealable plastic bag and crush them into fine crumbs with a rolling pin. Reserve ¼ cup of the crumbs for topping.

In a medium bowl, stir together the thawed whipped topping, milk, and vanilla extract until smooth.

Fold the remaining crushed cookies into the mixture.

Divide the mixture evenly among 8 popsicle molds.

Sprinkle the reserved cookie crumbs over the tops, then insert the popsicle sticks.

Freeze for at least 6 hours, or overnight, until completely firm.

To remove the popsicles, run the outside of the molds under warm water for 10–15 seconds. Gently pull on the sticks to release.

Serve immediately.