Losing an anchor rarely happens, but it does. My first diving ship was built in 1945. In letting the anchor chain go, it runs over the whelps (bumps) of the wildcat(reel) on an anchor windlass. Because of the maturity of the vessel, and the comparatively large number of cycles on the anchor, the whelps were worn down, so when the brake was applied, instead of the chain slowing down as the links engaged the whelps and spun on the wildcat, they just ran over them and kept on going! Pretty exciting!
Cleared the foc'sle out, except for a couple guys trying to apply the brake (to no avail). I recall a few things: (1) an enormous rust cloud as the chain got further into the chain locker and (2) there is no bolt on the end of the chain (for obvious reasons) and when the bitter end (last link) went out the hawsepipe (the hole in the ship where the anchor chain goes out) (3) all of the sudden it got eerily quiet, because it was incredibly noisy while all that was going on.
Fortunately, it wasn't in deep water and we put a couple guys over the side and picked it up.