Here are mine:
1 - I cut through a bullet felling a tree for my dad's neighbor. Nice and shiny where the saw went through it, but the chain cut fine, so I kept going.
2 - Years ago, cutting with my grandpa, I hit a lag bolt. Someone had fastened something to the tree, and the tree grew around it. Never saw it coming and broke the chain.
3 - Barbed wire fencing. Was helping a friend clear his fence line, didn't realize that the tree we were bucking used to be the fence line. They had moved the fence line about 20 feet, then this tree fell across it years later. This threw the chain off the bar. Had to clean up about 4 drive links with my flat file, but still have and use the chain to this day.
4 - Tomato cage. I was clearing some thumb sized brush with my chainsaw and didn't realize there was a tomato cage in all of it. That made a few sparks. No major damage, but lots of sparks.
5 - My all time favorite (because it happened to me last week and I am still trying to figure it out)...... CONCRETE. I cut down a poplar at the corner of our back yard and decided to cut the stump off level with the ground. It had a lot of butress roots, but I was just cutting away with a wedge supporting one side. Half way through the stump, the saw just quits cutting.........I said heck with it, I had felled, limbed, and bucked that tree with one saw, it must just be dull. Get my second saw, crank it and try to keep cutting. I go about an inch further, and it quits cutting. It was only then that I thoroughly inspected and found someone had throw a gob of concrete as big as a fist between two roots. It had been there a long time and blended right in with the tree. Busted that up, put on a fresh chain, and voila! Chains sharpened right back up and cut fine.
What have you hit with your saws? Ever break a chain?