You both have trials now.
It is not designed to handle that popup as during testing it couldn't reliably click it before a skeleton would attack, this could sometimes result in an endless loop till the player died or ran back to bank for food and repeated the process. You will need to disable to popup manually in game.
Please post your logger information, I should be able to see what the issue is with that.
Close and reboot your client, if the issue persists please post your logger info here so I can figure out what the issue seems to be.
There is both, the bot should be re-equipping any items in it's inventory if it dies did this happen once off or a few times?