Apparently, while writing this topic the objective has been completed. Seems to be quite a delay in registering the objective, enough so to leave the player wondering what's wrong. I mean, I was able to uncouple, couple again, uncouple, wondering what's wrong, get in the loco, release the brakes, move the loco a few yards, brake, walk to the coaches again, take screenshots, all while the objective was still not marked as complete.
I’ve noticed this in other routes with uncoupling objectives, which appear to have a time allocated to them before it moves to the next objective. It happens when dividing trains at Victoria in London Commuter as an example.
I had the same issue! on checking the times it was 2 minutes from the first time I uncoupled to the objective registering as complete.