Start by soaking the cedar plank in water for an hour while you preheat your @biggreenegg to 350°F setup for indirect cooking.
In a large bowl, combine the ground beef, breadcrumbs, Cabernet Sauvignon, chopped onion, minced garlic, eggs, milk, Worcestershire sauce, Dijon mustard, salt, pepper, and paprika. Mix well.
Next, form the mixture into a loaf shape then wrap with the bacon slices, tucking the ends underneath to secure. Place the bacon-wrapped meatloaf on the soaked cedar plank.
Now, place the cedar plank on the Big Green Egg and cook for about 1 hour.
In a small bowl, mix 1/4 cup ketchup, 2 tbsp Cabernet Sauvignon wine, and 1 tbsp brown sugar until well combined.
After the meatloaf has cooked for 1 hour, brush the glaze over the top. Continue cooking for another 15-20 minutes, or until the internal temperature of the meatloaf reaches 160°F and the bacon is crispy.
Remove the cedar plank with the meatloaf from the Big Green Egg and let it rest for 10 minutes before slicing.