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Step 1
Heat oven to 325 degrees Fahrenheit.
Step 2
In a large heavy skillet or saute pan, heat 1 tablespoon of oil over medium-high heat. While the oil is heating, toss beef cubes with flour and a generous pinch of salt in a large mixing bowl.
Step 3
When the oil is hot, brown the beef cubes. To get a golden-brown crust on the beef, be sure not to crowd the pan. Depending on the size of your pan, you may need to brown the beef in batches. Transfer the browned beef cubes to a Dutch oven or other heavy, oven-safe pot.
Step 4
Add the remaining tablespoon of oil to the same pan you used to brown the beef. Add diced onion, carrots, and celery to the pan. Season with a pinch of salt, and saute over medium-high heat for 5-6 minutes, or until vegetables are starting to soften and turn lightly brown at the edges.
Step 5
Add garlic to the vegetables and saute for 1 additional minute. Stir in smoked paprika, dried thyme, and tomato paste; cook for another 2 minutes. Add 2 cups of beef stock to the pan while scraping the bottom of the pan to loosen the brown bits. Remove from heat, and transfer mixture to the Dutch oven with the beef. (Everything is hot, so do this step carefully!)
Step 6
Add apple butter and apple cider vinegar to the beef and vegetables in the Dutch oven. Stir to combine. Cover with a tight-fitting lid, place in the heated oven and bake for 1 ½ hours.
Step 7
Remove from the oven. Add squash, potatoes, and remaining beef stock. Stir to combine. Replace lid and return to the oven for 1 hour.
Step 8
Remove from the oven. Stir and return to the oven without the lid in order to allow the liquid to reduce and thicken. Bake for 30 minutes, or until meat and vegetables are tender, and liquid is reduced to desired consistency.
Step 9
When the stew is done to your liking, remove from the oven and allow to cool slightly. Season to taste with salt and pepper before serving.