Actually you can, see: https://github.com/sferik/t/blob/7f1fcac61047dcb703e9519c837f7134fd7a7f57/lib/t/cli.rb#L843 https://github.com/sferik/t/blob/7f1fcac6104

Actually you can, see: https://github.com/sferik/t/blob/7f1fcac61047dcb703e9519c837f7134fd7a7f57/lib/t/cli.rb#L843 https://github.com/sferik/t/blob/7f1fcac61047dcb703e9519c837... this is because the OP's own twitter ruby gem can do that, this CLI app is basically a front end for the ruby gem client.update_with_media("I'm tweeting with @gem!", File.new("/path/to/media.png")) https://github.com/sferik/twitter/blob/48efb642beaa19355a4c1ba04a9fadac54cfba42/examples/Update.md#L40 https://github.com/sferik/twitter/blob/48efb642beaa19355a4c1...