Preheat the oven to 425 degrees F.

Cut the top and the bottom off of the acorn squash, trying to cut off as little as possible. Carefully slice the acorn squash into 5 rings, cutting the acorn squash from side to side (not from top to bottom).

Scrape the seeds and innards out of the rings and lay them flat on a baking sheet. Brush each ring with olive oil on both sides. Sprinkle sea salt over the top of the rings and place them in the preheated oven. Roast the squash rings for 30-35 minutes, flipping them over halfway through. The squash is done when it’s lightly brown and fork tender.

While the squash rings roast, heat the 1 1/2 teaspoons olive oil in a large skillet over medium heat. When the oil is hot, add the minced garlic and cook, stirring often until the garlic gets soft and is just starting to brown. Add the dried cranberries and chopped rosemary and cook for about 2 minutes more, until the rosemary is very fragrant and it smells like Christmas up in your kitchen.

Remove the herb-cranberry mixture to a bowl and add the ground beef to the skillet. Cook the ground beef just until no pink remains, then drain any excess fat.

Add the herb-cranberry mixture to the ground beef, as well as the 1 teaspoon salt, 1/8 teaspoon black pepper, and 1/2 teaspoon caraway. Stir to evenly combine.

When the squash rings have finished roasting, remove the baking sheet from the oven. Spoon the beef-cranberry mixture into each ring and place back in the oven. Cook for 4-5 minutes more.

Remove the baking sheet from the oven, top the stuffed squash with shredded parmesan cheese if desired, and enjoy!