Line a 9x5 inch baking dish with plastic wrap, letting some hang over the edges so it’ll form a sling from the icebox cake.
Finely chop 4 wafer cookies (we’ll use these for decorating the top of the cake).
Place the heavy cream, powdered sugar, and vanilla in the bowl of a stand mixer. Mix with the whisk attachment until light and fluffy, and soft peaks form.
Spread a thin layer of whipped cream into the bottom of the lined baking dish.
Top with a layer of chocolate wafer cookies, overlapping the cookies as necessary to cover the cream. Then add a thin layer of whipped cream, another layer of chocolate wafer cookies, then a layer of thinly sliced strawberries.
Repeat with whipped cream, wafer cookies, whipped cream, wafer cookies, and strawberries until the pan is filled.
Cover the top with plastic wrap.
Refrigerate for at least 4 hours, or overnight. Remove the plastic wrap from the pan, holding it like a sling, and invert the cake onto a serving platter.
Garnish the top with crumbled cookies, then use a sharp knife to cut the cake into slices. Serve immediately.