Chill the glasses: Place two tall glasses in the freezer for a few minutes while you prepare the drink. A cold glass keeps the blended frap thick longer.
Add ice and milk: Pour the ice cubes and whole milk into a blender. This ratio of ice to milk is what gives the drink its thick, snowy texture.
Add syrup and extract: Pour in the vanilla syrup and almond extract. The almond extract is what gives the drink its distinct sugar cookie flavor.
Blend until thick: Blend on high in short pulses until the mixture looks smooth and thick, about 30 to 45 seconds. Stop blending as soon as it holds a shape on a spoon.
Check the consistency: If the mixture is too thin, add a small handful of ice and blend again. If it's too thick to pour, add a splash more milk.
Drizzle the glass: Remove the chilled glasses from the freezer. Drizzle white chocolate sauce in a spiral pattern down the inside of each glass.
Rim with cookie crumbs: Dip the rim of each glass into crushed sugar cookies so the crumbs stick to the chocolate sauce.
Pour the drink: Pour the blended mixture into the prepared glasses, filling almost to the top.
Top with whipped cream: Add a generous swirl of whipped cream on top of each drink using a piping bag or spoon.
Garnish and serve: Sprinkle with red and green sprinkles and a few more crushed cookie crumbs. Serve with a wide straw right away.