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Prepare the Graham Cracker Crumbs
Combine the graham cracker crumbs, melted butter and sugar into a mixing bowl. Stir together until everything is combined.
Spoon about 4 tablespoons of the crumbs into the bottom of the mason jars.
Then using the tart tamper, gently press the crumbs into the bottom of the mason jars.
Set aside while you prepare the cheesecake pudding mixture.
Prepare the Cheesecake Pudding
In the bowl of the KitchenAid mixer, using the paddle attachment, cream together the softened cream cheese 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.
Place crumb mixture in the bottom of the jar and compress using the tart tamper. This is the base of the cheesecake.
Next add the cheesecake pudding mixture.
Set the jars in the refrigerator and allow to chill for up to 2 hours.
Remove from the refrigerator and add the cherry pie filling.