- Grate the squash (peeled, halved and seeded) through the large holes of a box grater.
- Heat oil in a large cast-iron or nonstick skillet over medium-low heat.
- Add chopped onion and minced garlic and cook, stirring, until soft and lightly colored, 10 to 12 minutes.
- Combine 2 tablespoons water and tomato paste in a small bowl and stir it into the pan.
- Add cooked brown rice and stir to coat.
- Add the squash, in batches if necessary, and stir until it has reduced in volume enough so that you can cover the pan.
- Increase the heat to medium-high, pour in 1 3/4 cups water (or broth) and wine, cover and bring to a boil.
- Reduce the heat to medium-low and cook, covered, stirring once or twice, until the rice has absorbed most of the liquid and the squash is tender, 25 to 30 minutes.
- Add chopped fennel fronds, fresh chopped oregano, salt, cinnamon and pepper; gently stir to combine. (Adjust seasoning according to taste)
- Remove from the heat and let stand, covered, for 5 minutes. Serve hot or at room temperature.