This is supposed to pop on Peninsula Corridor when reaching Level 20. I’m now Level 20 and no trophy yet. It’ll most probably pop at Level 21 instead (hopefully) but this is another example of a trophy not popping at the correct time.
I believe this is normal behaviour as it was in TSW2020. You have to complete the level rather than reach it. Just the wording is different. As long as it unlocks, I don't see any cause for concern.
So you now know you have to complete the level to get the trophy and won’t have to post a new thread every time this happens