Line an 8-inch cake pan with parchment paper.
In the bowl of a stand mixer fitted with the whisk attachment, add the heavy whipping cream, powdered sugar, and vanilla extract. Mix on low to avoid splattering, and gradually increase speed, until you’re at full speed and stiff peaks form.
Add about one third of the cookies to the prepared cake pan, making sure you have an even layer. You can crush them up by hand or just break them, this does not need to be perfect, just try to make it even.
Add half of the whipped cream frosting into the prepared cake pan and spread evenly. Drizzle a layer of caramel sauce and swirl around.
Repeat this process again, a layer one third of crushed up cookies, the second half of the whipped cream, and caramel sauce.
Then top the top of the cake with the remaining cookies and a drizzle of caramel sauce on top.
Place the cake pan in the fridge for at least 4 hours or overnight.
Remove cake from the pan and using a hot sharp knife, cut into slices and serve immediately.
Store leftover icebox cake in the fridge for 3 days, or in the freezer for up to 3 months (wrap in plastic wrap to keep fresh).