Spray 6-quart electric multicooker pot with PAM® Olive Oil No-Stick Cooking Spray. Select sauté function and heat until hot. Add onion to pot and cook until tender and starting to brown, about 5 minutes, stirring occasionally. Stir in garlic, red pepper flakes and oregano. Turn multicooker off.
Stir in Hunt's® Diced Tomatoes with their juice, broth, sugar, salt and pepper. Lock lid in place and close pressure release valve. Select high pressure cook function and set the timer for 8 minutes. While soup is cooking, make grilled cheese sandwiches.
To finish soup, allow for natural pressure release for 5 minutes before opening valve to release remaining steam. Puree soup with an immersion blender until smooth or carefully transfer soup to countertop blender and blend until smooth. Stir cream and basil into soup.
GRILLED CHEESE
Brush one side of each slice of bread with Wish-Bone® Italian dressing. Place cheese on 6 slices of bread (on the side that's been brushed with dressing). Top with a second slice of bread to make sandwiches, with the dressing on the inside. Spread butter on the outside of each sandwich.
Place sandwiches in air fryer in single layer. Air fry sandwiches in batches (if needed) at 350°F until bread is crispy and golden brown, 6 to 10 minutes, turning once.
Ladle tomato soup into bowls, sprinkle with Parmesan cheese if desired, and serve with grilled cheese sandwiches.