I keep getting this error when trying to provision a dropplet: The secure connection to the Digital Ocean API has failed. Please ensure that your local certificates directory is defined in the provider config. config.vm.provider :digital_ocean do |vm| vm.ca_path = "/path/to/ssl/ca/cert.crt" end This is generally caused by the OpenSSL configuration associated with the Ruby install being unaware of the system specific ca certs. I've already tried these solutions, but none seem to work: https://www.digitalocean.com/community/articles/how-to-use-digitalocean-as-your-provider-in-vagrant-on-an-ubuntu-12-10 https://gist.github.com/fnichol/867550