I am hitting probably the very same problem as well, right now. For more than 30 cycles, I have maintained green tick near the line "Dupes who completed Exosuit errands". Achievement not given. I even have a screenshot for each cycle, just to make sure each cycle was ticked.
Since the "All Dupes completed..." counter does not increase at all (~the same behavior as with "Easy livin" achievement), there is no way to track the progress. I consider that to be a bug (or very confusing design) as well. Some users report they were given the challenge, but I tried multiple times and no go.
My strategy was to lock all surviving dupes behind a checkpoint, giving them all day long mop duty each cycle. Lines were ticked after each cycle, but it did not unlock the challenge.
I am including my save file as well, with hope that someone will investigate. I am a challenge monger, after all, and just a few remaining.