Preheat the oven to 200°C (390°F). Line a baking sheet with parchment paper to prepare for roasting.
Using a paring knife, carefully make a slit lengthwise in each jalapeño, then gently open and remove most of the seeds for milder heat, or keep them if you like extra spice.
Brush the peppers lightly with olive oil and place them on the prepared baking sheet.
Roast the peppers in the oven for about 15-20 minutes, turning occasionally, until their skins blister and turn deep, smoky black in spots. You'll hear a gentle sizzling as they blister.
Remove the peppers from the oven and cover them with a clean towel or bowl for about 10 minutes. This steams the skins, making them easier to peel.
Gently peel off the blistered skins with your fingers or a paper towel, revealing the tender, smoky peppers underneath. Be careful—they'll be hot and soft.
Slice each pepper open lengthwise and remove any remaining seeds or membranes, then set aside in a bowl.
In a mixing bowl, combine the shredded cheddar, softened cream cheese, minced garlic, smoked paprika, cumin, and a pinch of salt. Mix until smooth and creamy, using a spoon or spatula.
Using a spoon, generously stuff each roasted pepper with the cheese mixture, pressing lightly to pack in the filling without spilling over.
Arrange the stuffed peppers on the baking sheet and bake for 12-15 minutes until the cheese is bubbly and golden around the edges.
For an extra crispy top, broil the poppers for 1-2 minutes, watching closely to prevent burning, until they develop a slight crackle and deepen in color.
Let the poppers rest for 5 minutes off the oven to allow the cheese to set. Serve warm, garnished with herbs if desired, and enjoy the smoky, cheesy bite.