This has happened twice, and I disclaim responsibility both times.
About 20 years ago I was in Australia and went to visit a friend. He wanted to go fishing so we went to pick up the boat from the shop where he had it serviced. We were going to launch it at a normal launch. He figured I was the better trailer driver, so he asked me to back the boat into the water. As we prepped it, I worked on the trailer and ensuring those connections were OK and all the lines were detached, and he worked on the boat. I backed it in and the boat floated off the trailer beautifully, for a few minutes. Then it sank down and sat on the trailer with plenty of water in the aft of the cockpit. I turned to him and asked if he happened to put the bilge plug. He looked at me quizzically and answered, “the what?”
It took 20 minutes for the water to drain out. I can’t ever figure out why it took so long.
Around 2009 or 2010 I moved my old Bayliner into the Drystack at Bayside Marine in Everett. The boat had been winter stored at my house and they were dewinterizing it and and putting it away in the dry stack. Mid May I called them in the evening to get it launched so I could go shrimping the next morning. I left a message and was pretty excited! First launch at the dry stack! Two hours later, they called me. “So, we have a bit of an issue. They called from the port and told us one of the boats at our dock was sitting low in the water…” Turns out, part of the dewinterizing routine hadn’t been to reinstall the bilge plug they had removed when they winterized the boat. The entire inboard/outdrive engine was submerged. It took them about a month to take everything apart, replace all the electronic bits and anything else that was damaged, and get it back in service. They did it right though and I stayed with them for 15 more years. They did all of it at no cost, and even replaced the damaged jump starter I had left in the lazarette.