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In a large glass bowl or container, whisk together brown sugar, molasses, soy sauce, rice vinegar, garlic, ginger, chili powder, ancho chile powder, olive oil and freshly ground black pepper until the sugar is dissolved.
Place tri-tip steaks in the marinade and turn until completely coated. Let marinate for about 1 to 2 hours, covered, turning the steak over halfway through.
When ready to cook, start the Traeger grill on Smoke with the lid open until the fire is established (4 to 5 minutes).
Place the steaks on the grill (do not discard the marinade). Smoke for 1 hour.
Remove steaks from grill and turn the heat up to High. Allow to preheat, lid closed, for 10 minutes.
Dip tri tip back into the marinade and put back on the Traeger and cook until the internal temp registers 130 degrees F, about 5 minutes per side, depending on the thickness of the tri tip.
Remove steak from the grill and let rest for 10 minutes before slicing.
Transfer the marinade and any juices collected from the cooked steaks to a small bowl. Heat them up in the microwave until it comes to a boil and then serve with the steak. Enjoy!