WARNING: Although your Ruby can connect to #{host} today, yo

Error message

WARNING: Although your Ruby can connect to #{host} today, your OpenSSL is very old!
WARNING: You will need to upgrade OpenSSL to use #{host}.

What it means

Error "WARNING: Although your Ruby can connect to #{host} today, your OpenSSL is very old! WARNING: You will need to upgrade OpenSSL to use #{host}." thrown in ruby/rubygems.

Source

Thrown at lib/bundler/cli/doctor/ssl.rb:137

      false
    end

    def warn_on_unsupported_tls12
      ctx = OpenSSL::SSL::SSLContext.new
      supported = true

      if ctx.respond_to?(:min_version=)
        begin
          ctx.min_version = ctx.max_version = OpenSSL::SSL::TLS1_2_VERSION
        rescue OpenSSL::SSL::SSLError, NameError
          supported = false
        end
      else
        supported = OpenSSL::SSL::SSLContext::METHODS.include?(:TLSv1_2) # rubocop:disable Naming/VariableNumber
      end

      Bundler.ui.warn(<<~EOM) unless supported

        WARNING: Although your Ruby can connect to #{host} today, your OpenSSL is very old!
        WARNING: You will need to upgrade OpenSSL to use #{host}.

      EOM
    end

    module Explanation
      extend self

      def explain_bundler_or_rubygems_error(error)
        case error.message
        when /certificate verify failed/
          "certificate verification"
        when /read server hello A/
          "SSL/TLS protocol version mismatch"
        when /tlsv1 alert protocol version/
          "requested TLS version is too old"

View on GitHub (pinned to 86cbb817a3)

Solutions

Upgrade OpenSSL (and relink/reinstall Ruby against it) before the host requires a newer TLS

When it happens

Trigger: Thrown at lib/bundler/cli/doctor/ssl.rb:137 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/2907949895a823a7. Report an issue: GitHub.