On a charter cat in St. Martin, we anchored in about 40 feet of water in Gustavia, St Bart's. The chain skipped off the chain gypsy and onto the rope drum, and ??? feet of 3/8 BBB started running out like crazy! It was loud and fast, and all we could do was to stand back, move away and wait until something broke -- I figured destruction was imminent. It being a charter cat I had no idea if the bitter end was secured or how, and even if it came out free I had great concern about the end whipping about as it went overboard. Everything stopped with a loud boom!
Amazingly, the chain wasn't lost overboard and nothing broke. When it got to the end it was tightly twisted and the resulting hockle couldn't clear the space behind the windlass, and it jammed between windlass and fiberglass frame. I put a dock line on the chain with a rolling hitch and using a mast winch -- was able to take tension off the jam and put the chain back on its proper gypsy to raise it. Observing the windlass after that I realized that if we didn't knock down the chain pile as the anchor was raised, on lowering it might cause the chain to feed onto the side of the gypsy, causing it to skip out; and apparently whoever had the boat before us hadn't done that. (Needless to say the charter company was informed of this situation).
It was frightening, and something I'll always remember.