In a mixing bowl, combine cream cheese, shredded cheddar cheese, and crumbled cooked bacon. Add garlic powder, kosher salt, and freshly ground black pepper. Mix until smooth.

Lay out an egg roll wrapper on a clean surface with a corner facing you. Place a halved pickle in the center and spoon about 2 tablespoons of the creamy filling on top. Fold the bottom corner over the filling, roll tightly, and tuck in the sides. Seal with water.

In a deep skillet, pour vegetable oil to a depth of about 2 inches and heat over medium heat to 350°F using a thermometer.

Carefully add a few assembled pickle egg rolls to the hot oil. Fry for 3-4 minutes on each side until golden brown. Keep an eye to prevent burning.

Remove fried egg rolls from the skillet and place on paper towels to drain excess oil. Sprinkle with chopped chives before serving. Serve with ranch dressing for dipping.