Make the Peanut Butter Cream: In a large bowl, beat the cream cheese, peanut butter, powdered sugar, and vanilla until smooth.
In a separate bowl, whip the heavy cream until stiff peaks form. Gently fold the whipped cream into the peanut butter mixture until light and fluffy. Set aside.
Make the Chocolate Soak: Whisk together the milk, cocoa powder, powdered sugar, and vanilla until smooth.
Assemble the Layers: Quickly dip each Nutter Butter into the chocolate mixture (don’t soak too long—they soften fast!).
Arrange a layer of dipped cookies in the bottom of a 9x9 dish. Spread half of the peanut butter cream over the top
Repeat with another layer of dipped cookies. Finish with the remaining cream layer
Make the Chocolate Ganache: Heat the heavy cream until just simmering, then pour over chocolate chips. Let sit for 2–3 minutes, then stir until smooth. Pour ganache over the top and spread evenly.
Cover and refrigerate for at least 4 hours, but overnight is best for that true tiramisu texture.
Top with crushed cookies, peanut butter cups, or a dusting of cocoa powder before serving.