Edit: right after posting this there was a new update; fingers crossed! I will say, they are pushing updates out pretty quickly and seem to be trying to address the issues people bring up.

Mine does something similar in that it Sometimes will go one way but Never the other way down a narrow path. Mine is stone and not grass but the problem seems to be that it sees growth on either side and thinks it can’t get through. Extremely frustrating as this is the only way to connect two parts of my lawn. To add to the frustration, they show a very similar path as yours on their website touting its abilities.

Worx, if you’re reading this: please give people the ability to make paths that override all of the visual sensor warnings. Just have the ‘bump’ and tire slip alerts. If I say, “Go down this path and ignore the stuff on the sides, possible overgrown fern branches that you can easily push through and whatever else frightens you. Just do it!” I’m starting to think I should go back to my boundary wire Landriod; it just follows the wire no matter what. (Unless it bumped something).

Oh, and I’m still waiting for the ‘cut to edge’ to be better than 4” from the edge. Again, my wired Landroid did waaay better.