01 - Cook elbow macaroni in boiling water according to package directions; drain and set aside. In a saucepan over medium heat, melt butter and whisk in flour. Cook for 1 minute, then gradually stir in milk until mixture thickens, about 2–3 minutes. Add shredded cheddar cheese, garlic powder, salt, and pepper; stir until smooth. Combine the cheese sauce with pasta and spread mixture onto a parchment-lined tray to chill in the refrigerator until firm, about 20 minutes.
02 - Slice each dill pickle into 1/2-inch thick rounds. Using a small round cutter or knife, remove the centers to create hollow rings. Pat the pickle rings completely dry with paper towels to prevent excess moisture.
03 - When the mac and cheese mixture is firm, press a portion into the center of each pickle ring, packing tightly. Arrange the filled rings on a tray and freeze for at least 15 minutes to maintain their structure during coating.
04 - Arrange three separate bowls: one with flour, a second with eggs beaten with 1 tablespoon milk, and a third with panko breadcrumbs mixed with paprika, cayenne (if desired), and salt. For each stuffed pickle ring, dredge in flour, dip in egg mixture, and coat in panko, pressing gently so the crumbs adhere.
05 - Heat vegetable oil in a deep fryer or heavy pot to 350°F (175°C). Fry the breaded pickle rings in batches for 2–3 minutes per side until crisp and golden. Remove using a slotted spoon and drain thoroughly on paper towels.
06 - Serve hot with dipping sauces such as ranch, spicy mayonnaise, or chipotle aioli.