Preheat the oven to 375°F.
Line a baking sheet with parchment paper.
Drain the baby dill pickles well.
Place the drained pickles on a paper towel-lined plate and allow them to dry while preparing the remaining ingredients.
In a small mixing bowl, combine the softened cream cheese, garlic powder, dried dill, and red pepper flakes.
Stir until the mixture is smooth and fully combined.
Unroll the crescent roll dough.
Separate the dough into individual triangles along the perforated lines.
Working with one crescent dough triangle at a time, place a small portion of the cream cheese mixture onto the wide end of the triangle.
Spread the cream cheese mixture slightly over the wide end of the dough.
Place one baby dill pickle on top of the cream cheese mixture.
Roll the dough from the wide end toward the pointed end, enclosing the pickle.
Place the roll seam-side down on the prepared baking sheet.
Repeat the process with the remaining crescent dough, cream cheese mixture, and pickles.
Arrange the rolls with space between each one to allow the dough to expand during baking.
Bake for 12 to 15 minutes, or until the crescent dough is golden brown and fully baked.
Remove the baking sheet from the oven.
Allow the rolls to cool for 10 to 15 minutes before serving, as the pickles will be very hot.
Serve warm with ranch dressing, if desired.