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Preheat your oven to 400°F (200°C) and line a baking sheet with parchment paper or lightly grease it.
Gently wipe the portobello mushrooms clean with a damp paper towel. Remove the stems and scrape out the dark gills.
Place the mushroom caps stem-side up on your baking sheet. Brush them lightly with olive oil, then sprinkle with salt and black pepper.
Pop them in the oven for 8-10 minutes to release excess moisture. Remove and pat any liquid dry with paper towels.
Spoon about 1-2 tablespoons of pesto into each mushroom cap and spread it evenly.
If using tomatoes, arrange the slices or halves on top of the pesto layer.
Sprinkle generously with mozzarella or lay slices over the top until covered.
Return the tray to the oven and bake for another 12-15 minutes until the cheese is melted and bubbly.
Switch your oven to broil on low for the final 2-3 minutes to achieve a crispy top.
Remove from the oven and let them rest for 3-5 minutes. Garnish with fresh basil leaves and balsamic glaze if desired.