Beef and Squash Chili

Toast chiles in a dry small skillet over medium-high heat, turning occasionally and pressing down to help them make contact with the pan, until darkened in color and beginning to soften, about 3 minutes. Transfer to a bowl and cover with 2 cups boiling water; let sit 30 minutes to soften. Drain; remove seeds and stems. Purée chiles and broth in a blender until smooth, about 1 minute.

Once chiles have soaked 10 minutes, heat 1 tablespoon oil in a large heavy pot over medium-high. Season beef with salt and pepper and cook, stirring occasionally, until browned all over, about 5 minutes. At this point, quite a bit of liquid will have accumulated; continue to cook until it has evaporated, about 3 minutes. Transfer beef to a plate.

Add 1 tablespoon oil to pot, then white onion and garlic; season with salt and pepper. Cook, stirring often, until softened, 6–8 minutes; onion juices will help loosen anything left on bottom of pot. Add cumin and oregano and cook, stirring, 1 minute.

Return beef to pot and add beer. Bring to a boil, reduce heat, and simmer, stirring occasionally, until almost completely reduced, about 4 minutes. Add chile purée, season with salt and pepper, and bring to a boil. Reduce heat and simmer until liquid is slightly thickened and meat is tender, 20–25 minutes. Add squash; cover and cook until tender, 10–15 minutes. Stir in lime juice.

Meanwhile, preheat oven to 350°F. Toss pumpkin seeds and remaining 1 teaspoon oil on a rimmed baking sheet; season with salt. Bake, stirring occasionally, until golden brown, 8–10 minutes. Let cool.

Serve chili topped with sour cream, avocado, red onion, and toasted pumpkin seeds.

Chili can be made 3 days ahead. Let cool; cover and chill, or freeze up to 1 month.