Step 1: Prepare the Cookie Crumbs

1. Place the chocolate sandwich cookies or chocolate wafer cookies into a food processor and pulse until finely crushed.
2. If you don't have a food processor, place the cookies in a sealed plastic bag and crush them with a rolling pin.
3. You want a fine crumb texture with a few slightly larger pieces for added crunch.

Step 2: Add the Butter

1. Transfer the crushed cookies to a bowl.
2. Pour in the melted butter and stir thoroughly until all the crumbs are lightly coated.
3. The mixture should resemble damp sand and hold together when gently pressed.

Step 3: Build the Cookie Base

1. Divide the cookie mixture evenly among six dessert jars.
2. Gently press the crumbs down using the back of a spoon.
3. Don't compact them too firmly because you want the base to remain easy to scoop.
4. Place the jars in the refrigerator while preparing the filling.

Step 4: Prepare the Cream Cheese Mixture

1. Place the softened cream cheese in a large mixing bowl.
2. Beat with an electric mixer for approximately 1–2 minutes until smooth and creamy.
3. Add the powdered sugar and cocoa powder.
4. Continue mixing until completely incorporated.

Step 5: Add the Chocolate Milk

1. Slowly pour the chilled chocolate milk into the cream cheese mixture while mixing on low speed.
2. Add the vanilla extract.
3. Beat until the mixture becomes smooth and evenly combined.
4. Avoid overmixing because excessive beating can make the mixture thinner than desired.

Step 6: Whip the Cream

1. In a separate chilled bowl, pour in the cold heavy whipping cream.
2. Beat on medium-high speed until soft peaks begin to form.
3. Continue beating carefully until firm peaks form.
4. Do not overwhip the cream, as it can become grainy.

Step 7: Fold the Whipped Cream Into the Chocolate Mixture

1. Add approximately one-third of the whipped cream to the chocolate cream cheese mixture.
2. Fold gently with a rubber spatula.
3. Add the remaining whipped cream in two additions, folding carefully after each addition.
4. The finished mixture should be light, creamy, and fluffy.

Step 8: Add Mini Chocolate Chips

1. If using mini chocolate chips, gently fold them into the chocolate filling.
2. Reserve a few for decorating the jars later.

Step 9: Add the First Cream Layer

1. Remove the cookie-base jars from the refrigerator.
2. Spoon or pipe a layer of chocolate milk whip filling over the cookie crumbs.
3. Fill each jar approximately one-third to halfway full.
4. Smooth the surface gently with a spoon.

Step 10: Add the Caramel

1. Drizzle approximately 1–2 tablespoons of caramel sauce over each chocolate layer.
2. For a visible swirl, use a toothpick or the tip of a small spoon to gently drag the caramel through the chocolate filling.
3. Avoid mixing completely because the contrast between chocolate and caramel creates the beautiful layered appearance.

Step 11: Add Another Cream Layer

1. Top the caramel with another layer of chocolate milk whip filling.
2. Leave enough space at the top of each jar for whipped cream and garnishes.

Step 12: Chill

1. Cover the jars loosely with lids or plastic wrap.
2. Refrigerate for at least 1 hour.
3. For an even firmer texture and deeper flavor, refrigerate for 2–4 hours.

Step 13: Decorate

1. Immediately before serving, add a small swirl of whipped cream to each jar.
2. Drizzle with additional caramel sauce.
3. Sprinkle with chocolate shavings, mini chocolate chips, and chopped pecans if desired.
4. For a salted caramel variation, finish with a very small pinch of flaky sea salt.

Step 14: Serve

1. Serve the dessert jars chilled with small dessert spoons.
2. The ideal bite combines the chocolate cookie base, fluffy chocolate cream, and caramel swirl.