This port depends on security/rubygem-net-ssh which has stricter defaults that OpenSSH: when using strict host key checking, security/rubygem-net-ssh will refuse the connexion if both the remote host name and IP address are not on the same line of a known_host file. security/rubygem-net-ssh added support for disabling strict host key checking in version 5.2.0, however this setting is still enabled by default because upstream OpenSSH has it enabled by default. However, FreeBSD ships with a modified version of OpenSSH where strict host key checking is disabled by default. As a result: - When adding an entry for a new host, only the host name is added in the known_host file; - The absence of CheckHostIP in the SSH configuration means the feature is disabled while such absence is generally the indication of the feature being enabled. As a consequence, host key verification may need additional work: - When using security/rubygem-net-ssh < 5.2.0, either: - Disable host key checking totally (--no-host-key-check parameter of the bolt command); - Update your remote host entries in the known_hosts file to use the format: , - When using security/rubygem-net-ssh >= 5.2.0 - Add "CheckHostIP no" to your SSH client configuration file (/etc/ssh/ssh_config or ~/.ssh/config). Some future version of security/rubygem-net-ssh should drop strict host key checking entirely, for more details, see: https://github.com/net-ssh/net-ssh/pull/663