In a medium bowl, whisk together the brown sugar, Italian dressing, and soy sauce until the sugar is mostly dissolved and the mixture looks smooth and glossy.
Pour the brown sugar mixture evenly over the pork chops in the slow cooker, making sure each chop is coated and some of the liquid settles underneath.
Cover and cook on LOW for 6–7 hours, or on HIGH for 3–4 hours, until the pork chops are very tender and nearly falling off the bone. Every slow cooker runs a bit differently, so start checking toward the earlier end of the range.
Once the pork is tender, carefully lift the chops out with a wide spatula or tongs, keeping them as intact as possible, and set them on a serving platter. They will be very soft.
Skim off any excess fat from the surface of the cooking liquid in the slow cooker. If you’d like a thicker, stickier glaze, turn the slow cooker to HIGH, leave the lid off, and let the sauce simmer for 10–15 minutes, stirring occasionally, until it reduces slightly and looks syrupy around the edges.
Spoon the glossy brown sugar sauce over the pork chops until they’re well coated and shiny. Serve immediately, passing extra sauce at the table for drizzling over sides.
Variations & Tips
For a slightly less sweet version, reduce the brown sugar to 3/4 cup and add an extra tablespoon of soy sauce to deepen the savory notes. If you like a touch of heat, stir 1/4 to 1/2 teaspoon of crushed red pepper flakes into the sauce before cooking.
Bone-in chops work best here for flavor and tenderness, but you can substitute thick-cut boneless pork chops; just start checking for doneness about 30 minutes earlier, as they can cook faster and risk drying out. To turn the sauce into a more gravy-like consistency, whisk 1 tablespoon of cornstarch with 1 tablespoon of cold water, then stir that slurry into the hot cooking liquid after you remove the pork; cook on HIGH with the lid off for 5–10 minutes until thickened.
If you’re cooking for a crowd, you can layer the pork chops slightly in the slow cooker—just be aware the ones on top may be a bit less saucy, so rotate them once halfway through if you’re home. Leftovers reheat well: store the pork in its sauce and gently warm on the stovetop over low heat or in the microwave at 50% power, adding a splash of water if needed to loosen the glaze.
