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Whisk together milk and sugar in a bowl until sugar is dissolved. Add heavy cream and vanilla; stir to combine. Transfer mixture to bowl of an electric ice cream maker. Freeze according to manufacturer's instructions. (Instructions and times will vary.)
Place 10 of the cookies in a ziplock plastic bag, and seal bag. Crush cookies using a rolling pin or meat mallet to a very fine, almost sandy, consistency. With ice cream machine running, add crushed cookies to thickened ice cream; continue freezing until fully incorporated, about 4 additional minutes. Remove bowl from ice cream maker; transfer ice cream to a 9- x 5-inch loaf pan.
Roughly chop remaining 8 cookies; sprinkle over ice cream in loaf pan, and fold gently to incorporate. Cover with plastic wrap; freeze in freezer 2 hours. Scoop with an ice cream scoop, and serve.