In the bowl of the KitchenAid mixer, using the paddle attachment, cream together the softened cream cheese and butter until smooth.

Add in the powdered sugar and vanilla and continue to mix until combined and smooth.

Switch out the paddle attachment for the whisk attachment, if you have one, and then add in the pudding mix followed by the milk.

Allow the pudding/cream cheese mixture to set until just firm. Since we're using instant pudding mix, this takes about 5 minutes.

Finally, fold in the container of Cool Whip.

Combine the graham cracker crumbs, melted butter and sugar into a mixing bowl. Stir together until everything is combined.

Spoon about 2 tablespoons of the crumbs into the bottom of the mason jars.

Reserve some of the crumbs to use as a garnish.

Then using the tart tamper, gently press the crumbs into the bottom of the cups.

Next, add the pudding/cream cheese mixture to the jars.

I found it easier to use a large cookie scoop to get the mixture into the cups without making a huge mess.

Add the strawberries, then top with the ReddiWip whipped cream and reserved graham cracker crumbs as a garnish.