Preheat the oil to 350°F in a deep stockpot or Dutch oven.
In a medium mixing bowl, beat together cream cheese, powdered sugar, and vanilla extract until thoroughly combined.
Add in Cool Whip and continue beating until mixture is smooth and fluffy.
Transfer mixture to a piping bag fitted with Tip #1M or a gallon-sized Ziploc bag. Set in the refrigerator to stay cold while preparing taco shells.
When the oil has reached a temperature of precisely 350°F, it’s time to fry the taco shells.
Using long-handled tongs (to keep your hands far away from the oil), pinch together two sides of a tortilla to form a folded taco shape. Holding the sides together, submerge the tortilla into the oil, frying for 1-2 minutes.
The tortilla will bubble up. If you lose your grip with the tongs, just use them to fold the taco back in half and keep it submerged to brown the inside and outside evenly.
When the tortilla is lightly browned, remove it from the oil and place directly in the tray of cinnamon sugar.
Use a spoon to sprinkle the cinnamon sugar evenly over the tortilla (inside and out) and then set on a paper-towel-lined inverted muffin tin to help the taco shells hold their shape while cooling.
When tacos shells are cooled, pipe a line of cheesecake filling across the center of the taco.
Top with 3 to 4 cherries (and sauce) from the can of pie filling.