Preheat the oven to 450 degrees. Toss the squash, oil, salt, and pepper and spread onto a baking sheet. Roast for 20 minutes. Remove from the oven and set aside.
Reduce the oven to 350 degrees and line a loaf pan with a parchment paper sling.
In a small bowl, whisk together the flaxseed and 3 tablespoons of water. Set aside to thicken.
While the squash is cooking, heat the coconut oil in a medium skillet. Add in the onions and celery, and sauté until the onions are translucent, about 7-10 minutes. Add in the garlic, thyme, rosemary, cinnamon, paprika, and white pepper. Sauté another 30 seconds, or until fragrant. Remove from the heat and set aside.
In a large bowl, add half the lentils, half the butternut squash, and the thickened flax mixture. Using a potato masher, mash the mixture until is resembles a paste. Add in all the remaining ingredients, and stir to combine.
Fill the lined loaf pan with the filling, pressing down on the top to compact it into the pan. Bake for 50 minutes.
While the loaf is baking, make the glaze. In a small saucepan, simmer the balsamic vinegar for 2-3 minutes, until slightly reduced. Remove from the heat and whisk in the remaining ingredients.
After 50 minutes of baking, remove the loaf from the oven and brush on the glaze. Return to the oven for 15 more minutes. Remove and allow to cool for at least 10 minutes before serving.
In a small saucepan, bring the balsamic vinegar to a boil. Simmer for about 2 minutes, or unitl the vinegar is slightly reduced. Remove from the heat and whisk in the remaining ingredients. Set aside.
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