MudRunner

If you're doing the maps on hardcore, you'll always have at least one truck with a crane in your convoy. When fully loaded, find a slope you can drive sideways on. The truck may tip on its own, or you may have to nudge it with another truck or with a winch to get it to fully tip. Once it does, the load will unpack and you can turn the truck upright with the other truck. Any logs that fall out can be picked up with the crane. Once all are loaded, pack the logs, and the achievement should pop.

Found a reliable way to do this with the Mount Logmore DLC map in casual mode, no crane or second truck needed.

• Recover the Freightliner FLD120 to the NW garage.

• Remove the semi hitch and add a log cart hitch and the long log cart.

• Follow the main road past the fuel station to the NE log station.

• Drive the truck into the log station, leaving the cart out (having the cart in the station area doesn't let the logs load).

• Load a set of long logs. Only 2 logs will appear.

• D-pad>Go to Advanced>d-pad toggle to pack the logs. The logs will bounce, and the achievement will unlock.

Please note, I did this from quick resume, and the achievement notified in game but did not unlock. I was able to quit out completely and repeat to unlock the achievement.