Separate the sandwich cookies and remove the filling from the middle with a butter knife. Discard the filling.
Place the cookies in a blender or food processor. Pulse the blender a few times to crush the cookies into fine crumbs. Set aside a small amount of the cookie crumbs for garnish and leave the rest in the blender.
Add the espresso, milk, one tablespoon of chocolate syrup and one tablespoon of chocolate chips to the blender with the cookie crumbs. Place the lid on top and blend the ingredients until smooth.
Remove the lid and add the ice. Blend the drink again until the ice is completely crushed and the ingredients are well mixed.
Place the mocha mixture in the freezer to chill for at least one hour, until it has slightly solidified.
When ready to serve, drizzle chocolate syrup along the inside of your glass, letting it drip to the bottom of the cup. Add the remaining chocolate chips to the cup, then pour the frozen Frappuccino into the glass. Drizzle more chocolate syrup over the top of the drink, add a dollop of whipped cream, and sprinkle the reserved cookie crumbs on top before serving.