Fully loaded tandem axle dump with pup trailer pulled off side road on to the highway, looked back, ran off the road, putting the truck and trailer on it’s roof. The pintle hitch broke and separated the units. I set up parallel with the trailer to keep one lane of traffic open and uprighted the trailer. Due to the steepness of the ditch, the truck being too close to the highway and to prevent any damage to the undamaged side, I setup in the ditch, lifted the front of the truck moving it about 15 feet further from the highway. I then setup parallel to the ditch and uprighted the truck. I then aired up the truck and pulled it 100 feet up the road so that I could winch the trailer to a flat spot and lift the tongue to install the jack. The trucking company sent a truck to pickup the trailer and I transported the truck to their yard. Total time from leaving the office to return was 4 hours and 49 miles round trip.