Preheat your oven to 400°F. While it heats, halve each acorn squash lengthwise and scoop out all the seeds with a sturdy spoon. Place the squash halves skin-side down on a baking sheet, then rub the cut surfaces generously with coconut oil and sprinkle with cinnamon. This initial roasting will soften the squash and allow the cinnamon to caramelize slightly, creating a subtle sweetness that complements the savory filling. Roast for 30-40 minutes until the flesh is very tender and easily pierced with a fork.

While the squash roasts, prepare your mise en place for the filling. Dice the yellow onion into 1/2-inch pieces, chop the celery into 1/4-inch pieces, and peel and dice the Granny Smith apple. I like to prep the apple last and keep it on the side—this prevents browning and ensures it stays firm and fresh-tasting when cooked. Measure out your sage, thyme, rosemary, salt, and the 2 tablespoons of cranberries and set them aside.

Heat a large skillet over medium-high heat. Add the ground pork and cook, breaking it apart with a wooden spoon, until deeply browned—about 5-7 minutes. This browning step is crucial for developing rich, savory flavors through the Maillard reaction. Once the pork is fully cooked and browned, transfer it to a plate, leaving about 2 tablespoons of the rendered fat in the pan. This fat becomes your flavor foundation for the vegetables.

Return the skillet to medium heat and add the diced onion to the reserved pork fat. Cook for 2-3 minutes until the onion becomes translucent and softens slightly. Add the chopped celery and diced apple, stirring frequently, and cook for another 3-4 minutes until the vegetables are tender but still maintain their shape. The apple will release moisture and add subtle sweetness that balances the herbs and savory pork beautifully.

Return the browned pork from Step 3 to the skillet with the sautéed vegetables and apple. Add the dried sage, thyme, rosemary, and sea salt, stirring everything together thoroughly. Let it cook for 1-2 minutes on medium heat so the dried herbs release their essential oils and fully distribute throughout the filling—you should smell the fragrant herb blend permeate the pan. Fold in the 2 tablespoons of cranberries, which will plump slightly and add tart notes that cut through the richness.

Remove the roasted squash from the oven—the flesh should be golden and very tender. Divide the warm pork filling evenly among the four squash halves, mounding it generously in the center. Top each filled squash with a few dried cranberries for garnish, which adds visual appeal and a final pop of tart sweetness. Serve immediately while the squash is still warm, as the filling will set slightly as it cools.