If you are playing on Wilderness mode and you die, Woby (and all of the items she's carrying) disappear. It makes sense that she should not remain and be accessible to other characters, but it makes her risky to use as a packmule. Other followers like Chester drop their items on death so you at least have a chance of recovering them; it would be helpful if the same was true of Woby.
1. Be Walter on Wilderness mode.
2. Be dumb and get killed by something.
3. Respawn and be sad that your Woby items are gone.