Obstructed attacks
You need to be in a plain surface (either leveled or higher than the enemy if it’s a slope) and facing it in order to #1 to work for sure.
That’s Arenanet’s way to say you should use staff. GS has been secretly nerfed, borked and bugged to a point it’s unviable. The only reason it’s still there it’s because it’s cool, so people keep paying for GS related stuff.
The serious issue of ranged attacks (especially mesmer Greatsword attacks) seemingly locking onto an area of the ‘hitbox’ of creatures that is below the surface (resulting in obstructed messages) has been brought to ArenaNet’s attention several times since the game went live (and I believe also during beta). ArenaNet chose to not only not fix the issue, but chose to not even acknowledge its existence or give any response regarding the issue at all.
Maybe they finally will to your reporting of the issue. Here’s to hoping.
In addition, they’ve also not fixed (nor acknowledged, I believe) the ‘line of sight’ issue for rifle and arrow shots from Rangers (though not sure about it existing for non-pet classes):
When the pet is positioned directly between the ranger and the target being fired upon, even though the projectile is seen to go far above the pet and actually strike the target, we are given a mixture of the ‘obstructed’ and ‘out of range’ error messages (even if the target is only feet away) due to the pet seemingly blocking the shot that actually went above its head.
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This behavior as noted by others above with the LOS issues in the game currently is also easily noticed when you use the Toy Soldier tonic. Try and launch fireworks (quick shot 1 or aimed shot 2) over people. The skill animation and ranged use always ends at the first character or object within the LOS. For ranged attacks, the LOS in the game is awful.