In a large electric frying pan over medium-high heat (350°F), cook onion and chopped jalapeno with olive oil, stirring often until softened, about 5 minutes.
Turn the heat down to medium-low (250°F) and carefully add the tomato passata, Tabasco and taco seasoning. Cook with the lid on for 15 mins. Turn the electric skillet off.
Remove the sauce from the skillet. Season with salt and pepper to taste, if needed. Spread ½ cup of the sauce in the bottom of the electric skillet and reserve the rest.
Take each tortilla individually and dip them into the reserved sauce until thinly coated on both sides (it is helpful to have the sauce in a shallow dish for this part). Fill with chicken breast, black olives and green onions (reserving some of the black olives and green onions for topping). Top with grated cheddar. Roll them up. Then place them in the electric skillet, seam-side down.
Repeat with the remaining tortillas. Pour whatever sauce is remaining on top. Sprinkle on the rest of the cheeses, jalapeno slices, green onions and black olives.
Cook the enchiladas covered at 300°F for 20 minutes, or until bubbly. Sprinkle chopped cilantro on top. Serve.