01 - Combine pumpkin purée, smoked paprika, cumin, cayenne pepper, salt, black pepper, and olive oil in a small bowl. Mix until smooth and thoroughly incorporated.
02 - Evenly spread the prepared pumpkin mixture onto two slices of bread.
03 - Arrange the sliced pickles over the pumpkin spread, then sprinkle the shredded cheddar cheese uniformly on top of the pickles.
04 - Place the remaining two slices of bread on top to form the sandwiches.
05 - Apply softened butter to the outer surfaces of each sandwich, covering both sides.
06 - Warm a nonstick skillet or griddle over medium heat.
07 - Cook the sandwiches for 3 to 4 minutes per side. Gently press with a spatula during cooking until the bread achieves a golden-brown exterior and the cheese is fully melted.
08 - Remove from heat, allow to cool briefly, slice in half, and serve immediately.