This achievement requires the player to deliver a load between specific countries in the Beyond the Baltic Sea dlc.
It doesn't matter which cargo, which type of truck, or in which order you do these routes. As long as you deliver cargo between the following countries without getting any damage, fines and if you're on time, you're gaining progress:
* Russia - Lithuania
* Lithuania - Latvia
* Latvia - Estonia
* Estonia - Russia
* Russia - Finland
These can be done like this, or the other way around. So for Russia - Finland, Finland - Russia also counts.
If you have real troubles with getting no fines, as sometimes speed limits suddenly change in cities for certain intersections, or because you forget to turn on your headlines, or overtaking took to long and the game registers it as wrong-way driving, you can turn off fines in the settings. The achievement can still be unlocked that way.