Start soaking the wooden toothpicks in a bowl of cold water for 15-20 minutes. Preheat the air fryer to 400 degrees F for 3-5 minutes.
Combine black pepper and ranch seasoning in a small bowl or ramekin and mix, then evenly spread seasoning onto a shallow plate. Wrap each pickle with one piece of bacon. Roll bacon-wrapped pickles in the seasoning.
Place pickles into the air fryer basket. Set cook time for 7 minutes to crisp up the bacon.
While that is cooking, lightly flour a wooden cutting board and roll out the puff pastry sheet into a 10x10” square. Cut into 1-inch strips, then cut each strip in half lengthwise.
Remove pickles from the air fryer and place them onto a wire rack lined baking sheet to cool for 5 minutes.
Preheat the air fryer to 385 degrees F, using the air fryer setting. Wrap each pickle with a strip of the puff pastry sheet. Brush with egg wash and sprinkle with sea salt.
Lightly spray the air fryer basket with nonstick cooking spray. Arrange pickles in a single layer evenly spaced in the basket and cook for 8 minutes, stopping once halfway through to flip.
Serve warm with dip, and enjoy!