When going to this specific spot in the Maze section of this parkour in the arcade hub, For some reason the game thinks you have crossed the checkpoint which is really behind the bushes, once you get the checkpoint this way though, it is impossible to continue with the parkour because the parkour thinks you have left the parkour area when you try to go to the actual checkpoint. Meaning you have to start at the beginning of the parkour again.
Edit: Sometimes you will have to go into the very corner of this dead end to get the Checkpoint to activate
This happens for me too. I think that the bounding box for the checkpoint is just too big (or if it’s a distance thing, the radius is too big). Like @JiMSUEE said, sometimes you have to go into the far corner to activate it (jumping in the corner might help too). The issue is that going around the correct way in the maze requires you to go so far that the parkour thinks you left.
I’d also like to note that this also allows a skip, if you activate the checkpoint and then use the “Return to last Checkpoint” item.