For dough: Put butternut squash in a medium pot with broth, scallion, adobo sauce, garlic, salt, and cumin. Bring to a simmer and cook until squash is tender, about 15 minutes.
Remove the squash with a slotted spoon, and reserve the broth. Set aside half of the squash for the filling, then mash the remaining squash is a large bowl. Mix in the masa with a fork. Slowly pour the seasoned broth over the filling, mixing with a fork (or hands) until smooth. Slowly stir in oils, a little at a time until dough is soft and moist. Cover with plastic wrap, set aside.
For filling: Heat the oil in a large skillet over medium heat. Add the scallions, garlic, chiles, cumin and salt and cook until soft, about 1 minute. Add reserved squash, olives, raisins, capers, and cook, stirring gently, until well combined, about 1 minute longer. Add broth and orange zest and cook, stirring occasionally until broth is slightly absorbed, about 2 minutes. Stir in cilantro, remove from heat.
To assemble: Cut 2 husks into 24-inch lengths about 1/2-inch wide. Place other soaked corn husks on cutting board, open side up. Place about a 1/4 cup dough in the center of each husk, leaving enough corn husk free to enclose tamale. Spoon 2 to 3 tablespoons filling on top. Then cover filling with about 2 to 3 tablespoons more of dough. Wrap the husks around the filling and twist and tie ends with reserved strips to make party favor shaped tamales.
Set up a 10-inch steamer basket. Lay tamales in steamer, cover and cook until the husks get slightly translucent, about 50 minutes. Remove tamales from steamer, and let rest for 5 to 10 minutes before serving with additional hot sauce if desired.