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In the bowl of the KitchenAid mixer, using the paddle attachment, cream together the softened cream cheese and butter until smooth.
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Add in the powdered sugar and vanilla and continue to mix until combined and smooth.
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Switch out the paddle attachment for the whisk attachment, if you have one, and then add in the pudding mix followed by the milk.
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Allow the pudding/cream cheese mixture to set until just firm. Since we're using instant pudding mix, this takes about 5 minutes.
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Finally, fold in the container of Cool Whip.
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Combine the graham cracker crumbs, melted butter and sugar into a mixing bowl. Stir together until everything is combined.
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Spoon about 2 tablespoons of the crumbs into the bottom of the mason jars.
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Reserve some of the crumbs to use as a garnish.
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Then using the tart tamper, gently press the crumbs into the bottom of the cups.
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Next, add the pudding/cream cheese mixture to the jars.
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I found it easier to use a large cookie scoop to get the mixture into the cups without making a huge mess.
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Add the blueberries, then top with the ReddiWip whipped cream and reserved graham cracker crumbs as a garnish.