With a mixer, beat the cream cheese until perfectly smooth. Add the powdered sugar and vanilla and mix well. Gradually pour in the whipping cream and then turn the mixer on high and beat until soft peaks form.
Add a layer of cookies in the bottom of a 9x13-inch baking dish. I used about 15 cookies on each layer plus about 5 broken cookies to fill in the space - for a total of 20 on each layer. (See the illustration on the website.)
Add about 1/3 of the whipped cream in dollops across the cookies. Spread it until it evenly covers the cookies. It may be necessary to hold the cookies in place with your other hand while you smooth the mixture over them. Once they're covered, the whipped cream will hold them in place.
Repeat with another layer of cookies, another layer of whipped cream, a 3rd layer of cookies, and top it with the last of the whipped cream. Crumble the remaining cookies over the top. Wrap tightly in plastic wrap and chill in the refrigerator at least 8 hours or overnight to allow the cookies to soften.
Once the cookies are soft, slice and serve. Keep refrigerated.
Making this recipe? Tag me on social media: @SouthernBite using the hashtag #SouthernBite so I can see what you're making! Find this recipe at https://southernbite.com/milk-and-cookies-icebox-cake/