In a medium bowl, combine the softened cream cheese and mayo, stirring until smooth and well blended. This creates the creamy foundation that helps bind all the flavors together. Add the shredded cheddar cheese and mix thoroughly until the cheese is evenly distributed throughout the mixture.
Add the minced fresh jalapeño and finely chopped pickled jalapeños to the cheese mixture from Step 1, stirring to combine. The fresh jalapeño provides bright heat and texture, while the pickled version adds tangy depth. Sprinkle in the garlic powder, smoked paprika, and salt, stirring until all seasonings are evenly incorporated throughout the filling.
Preheat your oven to 375°F. Arrange the phyllo shells on a baking sheet, keeping them in their natural cups. I like to spoon the filling generously into each shell—they can hold more than you'd think—then top each one with a pinch of the crumbled bacon for that savory, smoky element. Bake for 10-15 minutes until the filling is heated through and the phyllo edges turn golden brown and crispy.