Preheat the oven to 375ºF. In a large skillet over medium-high heat, add extra-virgin olive oil followed by the chicken breasts. Cook until golden brown on both sides, about 3 to 4 minutes per side. Remove from the pan and set aside. Add the onions, butternut squash, peppers, and tomatoes, and sauté until softened, about 5 minutes. Add in garlic, tomato paste, onion, powder, garlic powder, and salt until fragrant, about 1 minutes. Add in chicken bouillon and water and bring liquid to a simmer. Return chicken breasts to the pan, cover, and bake for 1 hour. Remove the pan from the oven allow to cool. Once cool enough to handle, shred the chicken using two forks then fold back into the mixture in the pan along with the dried cranberries and corn starch.
Working with one sheet of prepared dough at a time, gently roll it out to a size that will allow for about 5 pumpkins to be cut-out (reserve remaining dough and re-roll to cut out more pumpkins). Repeat this process until 24 pumpkins are cut. Cut out eyes and mouths on 12 of the pumpkin cut-outs. To the other 12 pumpkin cut-outs, add 1 to 2 Tbsp. of filling into the center of the dough. Gently brush the edges of the pumpkins with faces with egg wash then use them to top each pumpkin with filling. Using a fork, firmly press the edges together. Place formed Jack-o-nadas on a parchment-lined baking sheet.
Brush the top of each Jack-o-nada with egg wash then bake until golden brown, about 30-35 minutes. Allow to cool slightly before serving.
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