With more than a couple of years of messing with trees and chainsaws, I still get fooled. Yesterday I noticed a dead cherry along a fence that needs rebuilding. I figured I might was well drop it now rather than rebuilding the fence only to have the tree come down on it.
One branch of the cherry was under a branch of a neighboring tree but the connection didn't appear to be tight so I thought that as I dropped the tree, everything would just come loose. I made my hinge cut and back cut and while the tree leaned nicely, it didn't want to drop so I shoved a wedge in and tapped it. Gravity wasn't working so I pulled the wedge out and cut a bit more. Nope, still not enough help from gravity. I knew that the one branch couldn't be that much hold but that's the one reason the tree wasn't on the ground.
I could toss a cable over a fork so I did that and stretched it out behind another tree and gave it a tug and things came down just where they should. All was good until I looked up and noticed the branch from the neighboring tree was now split and hung in a third tree. I think the branch was actually being propped by the cut tree and when the cut tree came down the branch had enough of a defect to be weak.
It reminded me to always look up after dropping a tree- you never know what's ready to fall on your head. I looked at that tree several times from several angles but never figured the propped branch would be unstable.
You never know when dropping trees, even ones that appear simple.