Never happened before, luckily. A fair comment.
Once was another business who told me they'd accept the loss, but luckily a short while later the payment bounced back automatically.
Another time I used old details for an account which had been closed, that too bounced back (took 5-10 minutes to do so).
Finally I did send to old details for an advertisement, I'd not checked but to be fair to me in the past I'd found communication slow, difficult and often felt as if I was badgering/bothering/the responders had other lives.
In this case it was unrecoverable and the site bore the loss, although I did offer to send 50% because I did have the current details and should have deleted off the old ones. I've since deleted those details and always double check with everyone!
A couple of photographers I use require deposits upfront which I pay by transfer, every time I ask them for their details.