Pre-heat oven to 375°F.
Brush the bottom and sides of a 12-inch cast iron skillet, or other baking dish, with olive oil: set aside.
Cook bacon, on the stove top, in a large skillet until crispy.
Remove to paper towels to drain, then crumble.
Reserve 3 tbsp. drippings in skillet.
Cook ground beef and onion in bacon drippings, over medium-high heat, until no pink remains.
Add garlic and cook for 1 minute longer; drain excess fat from pan.
To the beef, add Worcestershire sauce, steak seasoning, salt and pepper; mix well and remove from heat.
Add soup, plus ½ soup can of milk, sour cream, ketchup, dill pickles, mustard and ½ cooked bacon; mix until fully combined.