Place eggs in a large pot, fill with water til eggs are just covered. Place on stove and set to boil. Once the water is at a full boil, set the timer for 10 minutes.
After the 10 minutes is up, turn off the stove but let the eggs sit a little longer.
Prepare a large bowl with ice and cold water to place the eggs in for easier peeling. Peel the eggs, being sure to rinse any shell pieces off.
With the paring knife, slice eggs in half. Place the yellow yolk in the large measuring bowl and set white halves in the tray. Repeat until all eggs are done.
Use the pastry cutter to thoroughly mash the egg yolks until there are no chunks.
Add mayo, mustard, sugar, and pickle juice to the yolks. Mix with spoon or spatula until it's fully combined and no dry bits of yolk are left.
Scoop yolk mixture into your cookie press and use the star burst tip. Use a swirl motion to fill the yolk mixture into the white egg halves.
Once all egg whites have had yolk mixture added to them, sprinkle a touch of paprika on top for a little extra flavor and beauty.