This is a winter version of my viral dumpling tomato salad (which I developed for NYT Cooking). I’ve roasted the tomatoes at high-ish temperatures, encouraging them to fall apart and surrender their hidden essence. A hint of sugar and salt encourages and enhances flavour. Once the tomatoes are feeling cozy, I add dumplings to the baking sheet and both are roasted together until the tomatoes collapse and the dumplings are crispy around the edges.
I used year round greenhouse grown tomatoes grown in Maine, a ‘cocktail’ size that is bigger than a cherry but smaller than a plum/roma tomato. They were actually very flavorful. If you prefer, you could also use canned whole tomatoes, draining the juices and just using the whole fruit.