Prep the mushrooms: Wipe the portobellos clean with a damp paper towel. Twist off the stems and gently scrape out the dark gills with a spoon. Pat dry thoroughly so they don’t steam.
Season the caps: Brush both sides with olive oil.
Sprinkle the insides with salt, black pepper, and minced garlic (or garlic powder). Add a small splash of balsamic vinegar inside each cap.
Preheat the air fryer: Set to 380°F (193°C) for 3 minutes. Preheating helps the mushrooms cook evenly and keeps them from getting soggy.
Start the mushrooms: Place the caps, cavity-side up, in the basket.
Air fry for 4–5 minutes to soften slightly and release some moisture.
Build the Caprese filling: Carefully remove the basket. Add mozzarella pieces to each cap, then scatter the tomatoes. Season with a pinch of salt, pepper, and dried oregano if using.
Melt and finish: Return to the air fryer for 4–6 minutes, until the cheese is melted and the tomatoes look juicy.
The edges of the mushrooms should be tender with lightly browned spots.
Top and serve: Transfer to plates. Add torn basil, a drizzle of balsamic glaze or a few drops of balsamic vinegar, and a little olive oil. Finish with red pepper flakes or Parmesan if you like.