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There is a button called something like Career Progress (don't know exatly how it is called in the english client).
It is the upper left button on the right side at the games desktop.
There you can hover over the grey dots and see what deliveries you have done.
Some of the deliveries for achievements are just very rare. So try again the next day and so on.
Can't say anything about this specific one though.
You can find loads to all the jobs, i have finish this achievements a couple of days ago. It take time and you just have to keep looking for the jobs, i did that i found them all in the Quickjob market. that was easier then i don't had to drive to each city in my own truck.
Here is a link to where you find the jobs to this achievements:
https://steamcommunity.com/sharedfiles/filedetails/?id=1580965545
The save file contains delivery_log_entry sections and within those params[2] is the name of the company delivered to and contains the target company and city names (unlike the in-game Progress History, which is useless in this instance because it doesn't show the company names only the cities).
As to the rarity of some of the jobs, the companies that you mention don't have a large number of incoming cargoes and thus those jobs are hard to find. As with many achievements, patience is the key. Sort the Freight Market by Recipient and check for jobs to those companies each time you look. Eventually something will show. Don't get frustrated when a job appears but not close enough for you to grab it (or use Quick Jobs - the job lists are the same) and just take them when possible. You will get there, others of us have done so.
@BCS: Thank you! I found that guide a while back and it have helped me.
The odd thing with the quick jobs that I did use for the farm deliveries didn't have the Industry standard deliveries at 8 in the morning. (I skip time and rest so I begin my "work day" at 8 so I always drive when it's day light because I might miss some of the landscape if its dark)
After reading that they do exist I tried skipping a few hours at a time and now I have completed a few. Still remains to find out which ones I have completed, more on this it my reply to The Pitts
@The Pitts: Thanks! I'll try finding a tool on the internet. I would like to use it not only for this but experimenting with the garages as you helped me with a few years ago (if you remember)
If I don't find a tool I have to draw blinds and see, I have logged my current deliveries in a spread sheet.
By the look of things it seem that Quick jobs and Freight market doesn't share the delivery pool, is that true?
For example I couldn't find a delivery in one city from a Quick job ini the Freight market.
I did look so it didn't expire in the Quick job list.
Next expansion(The Black sea) I will look into the achievements first and do any similar before doing the explorer.
The Enclave took me over 8 weeks to complete. I skipped time 4 hours to refresh the deliveries.
This was in all a gruesome and boring task...
But, thanks to all of you who got me confident that the deliveries still were there and that I had to lure the game to show me the goods (literally)
Now I have my personal achievement to discover 100% of the roads.