It has happened a couple of times with us but the last one was more recent and was discouraging as silver was not very responsive. We flew EIS-SJU ( stayed overnight as planned ) then onto Boston. drove home to Eastern Canada from there.
It was the Jet Blue staff who finally found our bags out back in a store room. silver had sent them to San Juan at some point but not sure when. They then delivered them fed ex 2 weeks later.
If you don’t mind potentially not having your stuff after a trip it’s not an issue. Just plan accordingly . Going is not so much of s big deal as silver will send them eventually they just have to find you .
Really travelling these days is not great fun but so worth it. Carry on is the way to go if you can swing it.
On a separate and really funny note we actually had two bags go missing in June from the ferry from Road Town to Charolette.
A real mystery…Mr Hodge from Road Town fast ferry was fantastic and called us to report they had fallen into the bilge when they opened a hatch to check on a potential leak! Oh the stories

he actually mailed them to us …for real