Bundler: failed (#{Explanation.explain_bundler_or_

Error message

Bundler:       failed     (#{Explanation.explain_bundler_or_rubygems_error(error)})

What it means

Error "Bundler: failed (#{Explanation.explain_bundler_or_rubygems_error(error)})" thrown in ruby/rubygems.

Source

Thrown at lib/bundler/cli/doctor/ssl.rb:83

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

    def bundler_connection_successful?
      Bundler.ui.info("\nTrying connections to #{uri}:\n")

      bundler_uri = Gem::URI(uri.to_s)
      Bundler::Fetcher.new(
        Bundler::Source::Rubygems::Remote.new(bundler_uri)
      ).send(:connection).request(bundler_uri)

      Bundler.ui.info("Bundler:       success")

      true
    rescue StandardError => error
      Bundler.ui.warn("Bundler:       failed     (#{Explanation.explain_bundler_or_rubygems_error(error)})")

      false
    end

    def rubygem_connection_successful?
      Gem::RemoteFetcher.fetcher.fetch_path(uri)
      Bundler.ui.info("RubyGems:      success")

      true
    rescue StandardError => error
      Bundler.ui.warn("RubyGems:      failed     (#{Explanation.explain_bundler_or_rubygems_error(error)})")

      false
    end

    def net_http_connection_successful?
      ::Gem::Net::HTTP.new(uri.host, uri.port).tap do |http|
        http.use_ssl = true

View on GitHub (pinned to 86cbb817a3)

Solutions

Follow the explanation in the output; typically update Bundler (`gem update bundler`) and RubyGems

When it happens

Trigger: Thrown at lib/bundler/cli/doctor/ssl.rb:83 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/1ed1fb285f92d7f2. Report an issue: GitHub.