Have not lost one yet.
We came pretty close once.
On a fishing outing several years ago, after doing some fishing (as opposed to "catching") in one spot for about an hour, we decided to find a better spot.
So I go to pull the anchor and find that I can pull in the line, but with a large amount of physical exertion.
I continued to work at it and was about wore out. Thinking that the anchor was not worth me pulling something (like an arm out of a socket), I asked Brenda to bring me a knife and was about to cut the line.
Just then, after pulling one last time, I could see that we had hooked a crab pot that must have been sitting on the bottom for several years. It was just about completely overgrown with barnacles, algae and whatever else.
I was able to tip the pointed end of the anchor down enough for the relic to slip off and back to a hopefully oblivious existence.
We keep a spare anchor on board.
