Oh no! Your Ruby doesn't have OpenSSL, so it can't connect t

Error message

Oh no! Your Ruby doesn't have OpenSSL, so it can't connect to #{host}.
You'll need to recompile or reinstall Ruby with OpenSSL support and try again.

What it means

Error "Oh no! Your Ruby doesn't have OpenSSL, so it can't connect to #{host}. You'll need to recompile or reinstall Ruby with OpenSSL support and try again." thrown in ruby/rubygems.

Source

Thrown at lib/bundler/cli/doctor/ssl.rb:53

      end
    end

    def verify_mode
      mode = @options[:"verify-mode"] || :peer

      @verify_mode ||= mode.then {|mod| OpenSSL::SSL.const_get("verify_#{mod}".upcase) }
    end

    def uri
      @uri ||= URI("https://#{host}")
    end

    def openssl_installed?
      require "openssl"

      true
    rescue LoadError
      Bundler.ui.warn(<<~MSG)
        Oh no! Your Ruby doesn't have OpenSSL, so it can't connect to #{host}.
        You'll need to recompile or reinstall Ruby with OpenSSL support and try again.
      MSG

      false
    end

    def output_ssl_environment
      Bundler.ui.info(<<~MESSAGE)
        Here's your OpenSSL environment:

        OpenSSL:       #{OpenSSL::VERSION}
        Compiled with: #{OpenSSL::OPENSSL_VERSION}
        Loaded with:   #{OpenSSL::OPENSSL_LIBRARY_VERSION}
      MESSAGE
    end

    def bundler_connection_successful?

View on GitHub (pinned to 86cbb817a3)

Solutions

Recompile or reinstall Ruby with OpenSSL support, then retry

When it happens

Trigger: Thrown at lib/bundler/cli/doctor/ssl.rb:53 when the library encounters an invalid state.

Common situations: See trigger scenarios.

AI-assisted analysis of ruby/rubygems@86cbb817a3 (2026-08-23). Data as JSON: /api/errors/ef60335c6e59a8e4. Report an issue: GitHub.