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Servers where sudo needs a password (e.g. Hatchbox-built hosts): upstate connect --observer=systemd, upstate observer upgrade and upstate observer switch now stage the files as your SSH user and print one command to run as root (sudo sh ~/.upstate-observer/install.sh or su -c ...). The CLI never handles a password; the token never appears on screen.
--ssh-user USER on connect and observer overrides Kamal's ssh.user for observer work (e.g. --ssh-user root).
SSH failures now show the real reason (for example sudo: a password is required).