Currently with chef-run targeting a RHEL6-like system, chef-run fails to connect when a command line like this is run
chef-run ssh://someone@somewhere SOME_COMMAND --password 1234 --sudo-password 1234
The reason is that this is the default setting in /etc/sudoers on RHEL6-like systems
chef-workstation 0.16.31 and above handles this situation better, and directs the user of the command how to change their /etc/sudoers.
If possible, it would be nice to work around this problem altogether, with no manual changes of system config files.