Preheat your oven to 425°F (220°C) and line a baking sheet with parchment paper. Arrange the halved, seeded jalapeños on the prepared sheet. Brush them on all sides with olive oil. Roast for about 15 minutes, or until their skins begin to char slightly. Remove from the oven and set aside to cool for a few minutes.
In a medium mixing bowl, combine the softened cream cheese, garlic salt, black pepper, and onion powder. Mix everything together until smooth and creamy. When the roasted jalapeños are cool enough to handle, roughly chop them and fold them into the cream cheese mixture. I like to keep some pieces a little chunky for extra texture and flavor.
Butter one side of each slice of bread (you'll use half the butter for this). On the unbuttered side of two bread slices, spread half of the cream cheese-jalapeño filling from Step 2. Sprinkle each with half the chopped bacon and 1/4 cup cheddar cheese per sandwich. Top each with another slice of bread, placing the buttered side facing out. Repeat for the second sandwich, using remaining filling, bacon, and cheese.
Heat a skillet over medium heat. Place the assembled sandwiches in the skillet and cook for 3–5 minutes per side, or until the bread is deeply golden and toasted and the cheese has melted inside. Press the sandwiches lightly with a spatula for even browning, and adjust the heat if the bread is browning too quickly. Serve immediately while hot. I love serving these sandwiches with a little hot sauce or a crunchy dill pickle on the side for extra kick.