Heat a non-stick pot. Add the onion and cook, stirring, until golden and beginning to brown (a pinch of baking soda will speed up this process). Add the bell pepper and jalapeno and cook until softened, about two minutes. Add the garlic, stir briefly, and then add tomatoes, beans, broth, and seasonings (but not squash or pineapple). Bring to a boil, then reduce heat and simmer for 15 minutes.
While the beans are cooking, trim the squash and cut into small cubes.
Add the squash and pineapple, increase the heat a little, and cover. Simmer until squash is just tender. Check seasonings, adding more to taste, and serve.
The crushed pineapple with juice causes this recipe to be 2 Weight Watchers points per serving on the Freestyle plan; if you drain the pineapple and don't use the juice, this is a zero point recipe (assuming your broth is also zero points.)