Preheat grill plates, a grill pan or a bbq on medium heat. Lightly grease grill plates with cooking oil.: You should hear a soft hiss when the surface is ready and feel the warmth when you carefully hover your hand above it, this signal means the pan is hot enough to sear without sticking. Preparing the grill surface prevents the mushrooms from tearing and ensures even caramelization along the edges, which gives a deeper savory flavor. A common mistake is using too low a heat, causing mushrooms to release moisture and steam rather than brown, so ensure the grill is truly medium hot. If oil starts to smoke, slightly lower the heat to prevent burning the butter later.
Combine the tomatoes, red onion, 2 tablespoons of the fresh basil, salt and pepper together in a medium-sized bowl. Mix until well combined. Set aside.: When you toss these together, you should smell the bright herbal aroma of basil and the sharp scent of red onion , while the tomatoes release a little juice that carries all flavors. This resting step allows the salt to draw out sweetness from the tomatoes, balancing acidity and enriching the topping, which will sit cold or room temperature on warm mushrooms for contrast. Avoid mixing too early if your tomatoes are very juicy, as the mixture can become watery; if that happens, drain a spoonful of liquid before topping the mushrooms.
Combine the garlic and butter and oregano together in a small saucepan (or microwave safe bowl), and melt until garlic is fragrant. Brush the each mushroom with garlic butter on all sides.: As the butter melts and the garlic releases its aroma, you ll notice a rich, savory scent that tells you the infusion is ready. Brushing the mushrooms evenly ensures the surface browns and absorbs flavor, creating a savory crust that contrasts with the juicy topping. One frequent issue is brushing too sparsely, which can leave dry spots that do not brown evenly; be generous and make sure the gill sides and rims get a good coating.
Grill for 5 minutes, until just beginning to soften.: You ll hear a steady sizzle and see the mushroom edges darken and slightly shrink as moisture evaporates, signaling they re ready to flip or remove. The flesh should be tender but still hold structure, offering a pleasant chew without collapsing. Because mushrooms vary in thickness, check the underside for golden brown patches rather than relying solely on time. A common error is overcooking until mushy, so aim for a slight firmness with browned edges.
When mushrooms are done, top with the tomato/basil mixture, and drizzle with the balsamic glaze. Sprinkle with a little extra salt, to your tastes, and garnish with the remixing basil leaves to serve.: The contrast between warm, butter kissed portobello mushrooms and the cool, zesty tomato mixture should be immediately apparent in aroma and texture, creating a satisfying interplay. Drizzling the glaze adds glossy sweetness that brightens the savory base, and the final sprinkle of salt sharpens flavors. Avoid piling on too much topping at once which can weigh the mushroom down and make it hard to serve; offer the tomato mix in a moderate spoonful so every bite stays balanced.
(If making from scratch, prepare while mushrooms are grilling.) Combine sugar (if using) and vinegar in a small saucepan over high heat and bring to the boil. Reduce heat to low; allow to simmer for 5-8 minutes or until mixture has thickened and reduced to a glaze. (If not using sugar, allow to reduce for 12-15 minutes on low heat.): As the vinegar reduces you ll notice steam and a fragrant, tangy scent transform into a syrupy aroma with hints of caramel when sugar is present, and the volume will shrink noticeably. This concentrated glaze will cling to the mushroom and tomato, adding both sheen and flavor depth. A common pitfall is leaving it unattended which can quickly burn the sugars, so watch the saucepan and stir occasionally to ensure even reduction and prevent scorching.
Preheat oven to grill/broil settings on high heat. Arrange oven shelf to the middle of your oven. Follow the directions above to prepare your mushrooms with the garlic butter. Place them, buttered side down, on a baking tray. Grill/broil until for about 8 minutes, until mushrooms begin to brown. Once cooked, continue with directions above.: Under the broiler you ll see the mushroom surfaces bubble and darken, and you may hear a faint crackle as edges brown; these are visual cues the caramelization process is happening. This oven method is a reliable indoor alternative to grilling, producing a similar texture and flavor, though the timing can vary with oven intensity. A common issue is placing the tray too close to the heat which can char the mushrooms before the centers cook; keep the shelf in the middle and monitor closely to achieve even browning without burning.