Merge RubyGems 3.2.26 and Bundler 2.2.26

39 files changed, 475 insertions, 282 deletions

diff --git a/lib/bundler/cli.rb b/lib/bundler/cli.rb
index f054a2bfed..294b07d555 100644
--- a/lib/bundler/cli.rb
+++ b/lib/bundler/cli.rb
@@ -73,14 +73,6 @@ module Bundler
       Bundler.ui = UI::Shell.new(options)
       Bundler.ui.level = "debug" if options["verbose"]
       unprinted_warnings.each {|w| Bundler.ui.warn(w) }
-
-      if ENV["RUBYGEMS_GEMDEPS"] && !ENV["RUBYGEMS_GEMDEPS"].empty?
-        Bundler.ui.warn(
-          "The RUBYGEMS_GEMDEPS environment variable is set. This enables RubyGems' " \
-          "experimental Gemfile mode, which may conflict with Bundler and cause unexpected errors. " \
-          "To remove this warning, unset RUBYGEMS_GEMDEPS.", :wrap => true
-        )
-      end
     end
 
     check_unknown_options!(:except => [:config, :exec])
@@ -469,7 +461,7 @@ module Bundler
     map aliases_for("cache")
 
     desc "exec [OPTIONS]", "Run the command in context of the bundle"
-    method_option :keep_file_descriptors, :type => :boolean, :default => false
+    method_option :keep_file_descriptors, :type => :boolean, :default => true
     method_option :gemfile, :type => :string, :required => false
     long_desc <<-D
       Exec runs a command, providing it access to the gems in the bundle. While using
@@ -477,6 +469,10 @@ module Bundler
       into the system wide RubyGems repository.
     D
     def exec(*args)
+      if ARGV.include?("--no-keep-file-descriptors")
+        SharedHelpers.major_deprecation(2, "The `--no-keep-file-descriptors` has been deprecated. `bundle exec` no longer mess with your file descriptors. Close them in the exec'd script if you need to")
+      end
+
       require_relative "cli/exec"
       Exec.new(options, args).run
     end
diff --git a/lib/bundler/cli/check.rb b/lib/bundler/cli/check.rb
index 65c51337d2..4221fc7f2b 100644
--- a/lib/bundler/cli/check.rb
+++ b/lib/bundler/cli/check.rb
@@ -15,7 +15,7 @@ module Bundler
       definition.validate_runtime!
 
       begin
-        definition.resolve_only_locally!
+        definition.resolve_with_cache!
         not_installed = definition.missing_specs
       rescue GemNotFound, VersionConflict
         Bundler.ui.error "Bundler can't satisfy your Gemfile's dependencies."
diff --git a/lib/bundler/cli/exec.rb b/lib/bundler/cli/exec.rb
index 318d57fb06..42b602a055 100644
--- a/lib/bundler/cli/exec.rb
+++ b/lib/bundler/cli/exec.rb
@@ -12,12 +12,7 @@ module Bundler
       @options = options
       @cmd = args.shift
       @args = args
-
-      if !Bundler.current_ruby.jruby?
-        @args << { :close_others => !options.keep_file_descriptors? }
-      elsif options.keep_file_descriptors?
-        Bundler.ui.warn "Ruby version #{RUBY_VERSION} defaults to keeping non-standard file descriptors on Kernel#exec."
-      end
+      @args << { :close_others => !options.keep_file_descriptors? } unless Bundler.current_ruby.jruby?
     end
 
     def run
diff --git a/lib/bundler/cli/gem.rb b/lib/bundler/cli/gem.rb
index eb1119859c..b3bb025b89 100644
--- a/lib/bundler/cli/gem.rb
+++ b/lib/bundler/cli/gem.rb
@@ -184,14 +184,15 @@ module Bundler
         )
       end
 
-      if File.exist?(target) && !File.directory?(target)
+      if target.exist? && !target.directory?
         Bundler.ui.error "Couldn't create a new gem named `#{gem_name}` because there's an existing file named `#{gem_name}`."
         exit Bundler::BundlerError.all_errors[Bundler::GenericSystemCallError]
       end
 
       if use_git
         Bundler.ui.info "Initializing git repo in #{target}"
-        `git init #{target}`
+        require "shellwords"
+        `git init #{target.to_s.shellescape}`
 
         config[:git_default_branch] = File.read("#{target}/.git/HEAD").split("/").last.chomp
       end
diff --git a/lib/bundler/definition.rb b/lib/bundler/definition.rb
index f987d85f5b..673bf37698 100644
--- a/lib/bundler/definition.rb
+++ b/lib/bundler/definition.rb
@@ -161,12 +161,6 @@ module Bundler
       @multisource_allowed
     end
 
-    def resolve_only_locally!
-      @remote = false
-      sources.local_only!
-      resolve
-    end
-
     def resolve_with_cache!
       sources.cached!
       resolve
@@ -505,7 +499,7 @@ module Bundler
     end
 
     def precompute_source_requirements_for_indirect_dependencies?
-      sources.non_global_rubygems_sources.all?(&:dependency_api_available?) && !sources.aggregate_global_source?
+      @remote && sources.non_global_rubygems_sources.all?(&:dependency_api_available?) && !sources.aggregate_global_source?
     end
 
     def current_ruby_platform_locked?
diff --git a/lib/bundler/dsl.rb b/lib/bundler/dsl.rb
index 3517a109ed..ed7b3e2d6b 100644
--- a/lib/bundler/dsl.rb
+++ b/lib/bundler/dsl.rb
@@ -457,7 +457,7 @@ repo_name ||= user_name
     def implicit_global_source_warning
       Bundler::SharedHelpers.major_deprecation 2, "This Gemfile does not include an explicit global source. " \
         "Not using an explicit global source may result in a different lockfile being generated depending on " \
-        "the gems you have installed locally before bundler is run." \
+        "the gems you have installed locally before bundler is run. " \
         "Instead, define a global source in your Gemfile like this: source \"https://rubygems.org\"."
     end
 
diff --git a/lib/bundler/errors.rb b/lib/bundler/errors.rb
index 11763b4e88..565aaeeb9d 100644
--- a/lib/bundler/errors.rb
+++ b/lib/bundler/errors.rb
@@ -122,7 +122,7 @@ module Bundler
 
   class VirtualProtocolError < BundlerError
     def message
-      "There was an error relating to virtualization and file access." \
+      "There was an error relating to virtualization and file access. " \
       "It is likely that you need to grant access to or mount some file system correctly."
     end
 
diff --git a/lib/bundler/installer/standalone.rb b/lib/bundler/installer/standalone.rb
index f16135cb48..e8494b4bcd 100644
--- a/lib/bundler/installer/standalone.rb
+++ b/lib/bundler/installer/standalone.rb
@@ -12,12 +12,13 @@ module Bundler
       end
       File.open File.join(bundler_path, "setup.rb"), "w" do |file|
         file.puts "require 'rbconfig'"
-        file.puts "ruby_engine = RUBY_ENGINE"
-        file.puts "ruby_version = RbConfig::CONFIG[\"ruby_version\"]"
-        file.puts "path = File.expand_path('..', __FILE__)"
         file.puts reverse_rubygems_kernel_mixin
         paths.each do |path|
-          file.puts %($:.unshift File.expand_path("\#{path}/#{path}"))
+          if Pathname.new(path).absolute?
+            file.puts %($:.unshift "#{path}")
+          else
+            file.puts %($:.unshift File.expand_path("\#{__dir__}/#{path}"))
+          end
         end
       end
     end
@@ -28,14 +29,14 @@ module Bundler
       @specs.map do |spec|
         next if spec.name == "bundler"
         Array(spec.require_paths).map do |path|
-          gem_path(path, spec).sub(version_dir, '#{ruby_engine}/#{ruby_version}')
+          gem_path(path, spec).sub(version_dir, '#{RUBY_ENGINE}/#{RbConfig::CONFIG["ruby_version"]}')
           # This is a static string intentionally. It's interpolated at a later time.
         end
-      end.flatten
+      end.flatten.compact
     end
 
     def version_dir
-      "#{Bundler::RubyVersion.system.engine}/#{RbConfig::CONFIG["ruby_version"]}"
+      "#{RUBY_ENGINE}/#{RbConfig::CONFIG["ruby_version"]}"
     end
 
     def bundler_path
@@ -44,7 +45,11 @@ module Bundler
 
     def gem_path(path, spec)
       full_path = Pathname.new(path).absolute? ? path : File.join(spec.full_gem_path, path)
-      Pathname.new(full_path).relative_path_from(Bundler.root.join(bundler_path)).to_s
+      if spec.source.instance_of?(Source::Path)
+        full_path
+      else
+        Pathname.new(full_path).relative_path_from(Bundler.root.join(bundler_path)).to_s
+      end
     rescue TypeError
       error_message = "#{spec.name} #{spec.version} has an invalid gemspec"
       raise Gem::InvalidSpecificationException.new(error_message)
diff --git a/lib/bundler/resolver.rb b/lib/bundler/resolver.rb
index a78b2db157..d26e2feb10 100644
--- a/lib/bundler/resolver.rb
+++ b/lib/bundler/resolver.rb
@@ -255,12 +255,6 @@ module Bundler
         next if name == "bundler"
         next unless search_for(requirement).empty?
 
-        cache_message = begin
-                            " or in gems cached in #{Bundler.settings.app_cache_path}" if Bundler.app_cache.exist?
-                          rescue GemfileNotFound
-                            nil
-                          end
-
         if (base = @base[name]) && !base.empty?
           version = base.first.version
           message = "You have requested:\n" \
@@ -269,18 +263,17 @@ module Bundler
             "Try running `bundle update #{name}`\n\n" \
             "If you are updating multiple gems in your Gemfile at once,\n" \
             "try passing them all to `bundle update`"
-        elsif source = @source_requirements[name]
+        else
+          source = source_for(name)
           specs = source.specs.search(name)
           versions_with_platforms = specs.map {|s| [s.version, s.platform] }
-          message = String.new("Could not find gem '#{SharedHelpers.pretty_dependency(requirement)}' in #{source}#{cache_message}.\n")
-          message << if versions_with_platforms.any?
-            "The source contains the following versions of '#{name}': #{formatted_versions_with_platforms(versions_with_platforms)}"
-          else
-            "The source does not contain any versions of '#{name}'"
-          end
-        else
-          message = "Could not find gem '#{SharedHelpers.pretty_dependency(requirement)}' in any of the gem sources " \
-            "listed in your Gemfile#{cache_message}."
+          cache_message = begin
+                              " or in gems cached in #{Bundler.settings.app_cache_path}" if Bundler.app_cache.exist?
+                            rescue GemfileNotFound
+                              nil
+                            end
+          message = String.new("Could not find gem '#{SharedHelpers.pretty_dependency(requirement)}' in #{source.to_err}#{cache_message}.\n")
+          message << "The source contains the following versions of '#{name}': #{formatted_versions_with_platforms(versions_with_platforms)}" if versions_with_platforms.any?
         end
         raise GemNotFound, message
       end
@@ -378,7 +371,7 @@ module Bundler
             o << if metadata_requirement
               "is not available in #{relevant_source}"
             else
-              "in #{relevant_source}.\n"
+              "in #{relevant_source.to_err}.\n"
             end
           end
         end,
diff --git a/lib/bundler/settings.rb b/lib/bundler/settings.rb
index 03126f616c..abf7db21b4 100644
--- a/lib/bundler/settings.rb
+++ b/lib/bundler/settings.rb
@@ -430,6 +430,8 @@ module Bundler
         Pathname.new(ENV["BUNDLE_CONFIG"])
       elsif ENV["BUNDLE_USER_CONFIG"] && !ENV["BUNDLE_USER_CONFIG"].empty?
         Pathname.new(ENV["BUNDLE_USER_CONFIG"])
+      elsif ENV["BUNDLE_USER_HOME"] && !ENV["BUNDLE_USER_HOME"].empty?
+        Pathname.new(ENV["BUNDLE_USER_HOME"]).join("config")
       elsif Bundler.rubygems.user_home && !Bundler.rubygems.user_home.empty?
         Pathname.new(Bundler.rubygems.user_home).join(".bundle/config")
       end
diff --git a/lib/bundler/source.rb b/lib/bundler/source.rb
index 5388a7681e..7bf493d73d 100644
--- a/lib/bundler/source.rb
+++ b/lib/bundler/source.rb
@@ -36,8 +36,6 @@ module Bundler
 
     def local!; end
 
-    def local_only!; end
-
     def cached!; end
 
     def remote!; end
@@ -67,6 +65,10 @@ module Bundler
       "#<#{self.class}:0x#{object_id} #{self}>"
     end
 
+    def to_err
+      to_s
+    end
+
     def path?
       instance_of?(Bundler::Source::Path)
     end
diff --git a/lib/bundler/source/rubygems.rb b/lib/bundler/source/rubygems.rb
index 858a69a48b..298ff98e24 100644
--- a/lib/bundler/source/rubygems.rb
+++ b/lib/bundler/source/rubygems.rb
@@ -26,12 +26,6 @@ module Bundler
         Array(options["remotes"]).reverse_each {|r| add_remote(r) }
       end
 
-      def local_only!
-        @specs = nil
-        @allow_local = true
-        @allow_remote = false
-      end
-
       def local!
         return if @allow_local
 
@@ -50,6 +44,7 @@ module Bundler
         return if @allow_cached
 
         @specs = nil
+        @allow_local = true
         @allow_cached = true
       end
 
@@ -96,11 +91,22 @@ module Bundler
         out << "  specs:\n"
       end
 
+      def to_err
+        if remotes.empty?
+          "locally installed gems"
+        elsif @allow_remote
+          "rubygems repository #{remote_names} or installed locally"
+        elsif @allow_cached
+          "cached gems from rubygems repository #{remote_names} or installed locally"
+        else
+          "locally installed gems"
+        end
+      end
+
       def to_s
         if remotes.empty?
           "locally installed gems"
         else
-          remote_names = remotes.map(&:to_s).join(", ")
           "rubygems repository #{remote_names} or installed locally"
         end
       end
@@ -319,6 +325,10 @@ module Bundler
 
       protected
 
+      def remote_names
+        remotes.map(&:to_s).join(", ")
+      end
+
       def credless_remotes
         remotes.map(&method(:suppress_configured_credentials))
       end
diff --git a/lib/bundler/source/rubygems_aggregate.rb b/lib/bundler/source/rubygems_aggregate.rb
index 685bf7e90a..09cf4002ea 100644
--- a/lib/bundler/source/rubygems_aggregate.rb
+++ b/lib/bundler/source/rubygems_aggregate.rb
@@ -16,6 +16,10 @@ module Bundler
         @index
       end
 
+      def to_err
+        to_s
+      end
+
       def to_s
         "any of the sources"
       end
diff --git a/lib/bundler/source_list.rb b/lib/bundler/source_list.rb
index d6310b78c0..b97206f497 100644
--- a/lib/bundler/source_list.rb
+++ b/lib/bundler/source_list.rb
@@ -136,10 +136,6 @@ module Bundler
       different_sources?(lock_sources, replacement_sources)
     end
 
-    def local_only!
-      all_sources.each(&:local_only!)
-    end
-
     def cached!
       all_sources.each(&:cached!)
     end
diff --git a/lib/bundler/templates/newgem/github/workflows/main.yml.tt b/lib/bundler/templates/newgem/github/workflows/main.yml.tt
index 654978033f..83ddea25dc 100644
--- a/lib/bundler/templates/newgem/github/workflows/main.yml.tt
+++ b/lib/bundler/templates/newgem/github/workflows/main.yml.tt
@@ -1,16 +1,26 @@
 name: Ruby
 
-on: [push,pull_request]
+on:
+  push:
+    - <%= config[:git_default_branch] %>
+
+  pull_request:
 
 jobs:
   build:
     runs-on: ubuntu-latest
+
+    strategy:
+      matrix:
+        ruby:
+          - <%= RUBY_VERSION %>
+
     steps:
     - uses: actions/checkout@v2
     - name: Set up Ruby
       uses: ruby/setup-ruby@v1
       with:
-        ruby-version: <%= RUBY_VERSION %>
+        ruby-version: ${{ matrix.ruby }}
         bundler-cache: true
     - name: Run the default task
       run: bundle exec rake
diff --git a/lib/bundler/templates/newgem/newgem.gemspec.tt b/lib/bundler/templates/newgem/newgem.gemspec.tt
index 91ce856bff..271d39dec5 100644
--- a/lib/bundler/templates/newgem/newgem.gemspec.tt
+++ b/lib/bundler/templates/newgem/newgem.gemspec.tt
@@ -25,7 +25,9 @@ Gem::Specification.new do |spec|
   # Specify which files should be added to the gem when it is released.
   # The `git ls-files -z` loads the files in the RubyGem that have been added into git.
   spec.files = Dir.chdir(File.expand_path(__dir__)) do
-    `git ls-files -z`.split("\x0").reject { |f| f.match(%r{\A(?:test|spec|features)/}) }
+    `git ls-files -z`.split("\x0").reject do |f|
+      (f == __FILE__) || f.match(%r{\A(?:(?:test|spec|features)/|\.(?:git|travis|circleci)|appveyor)})
+    end
   end
   spec.bindir        = "exe"
   spec.executables   = spec.files.grep(%r{\Aexe/}) { |f| File.basename(f) }
diff --git a/lib/bundler/version.rb b/lib/bundler/version.rb
index 4447aa401e..510953c543 100644
--- a/lib/bundler/version.rb
+++ b/lib/bundler/version.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: false
 
 module Bundler
-  VERSION = "2.2.25".freeze
+  VERSION = "2.2.26".freeze
 
   def self.bundler_major_version
     @bundler_major_version ||= VERSION.split(".").first.to_i
diff --git a/lib/rubygems.rb b/lib/rubygems.rb
index 900f98542e..8f46264d93 100644
--- a/lib/rubygems.rb
+++ b/lib/rubygems.rb
@@ -8,7 +8,7 @@
 require 'rbconfig'
 
 module Gem
-  VERSION = "3.2.25".freeze
+  VERSION = "3.2.26".freeze
 end
 
 # Must be first since it unloads the prelude from 1.9.2
@@ -249,9 +249,6 @@ module Gem
   # you to specify specific gem versions.
 
   def self.bin_path(name, exec_name = nil, *requirements)
-    # TODO: fails test_self_bin_path_bin_file_gone_in_latest
-    # Gem::Specification.find_by_name(name, *requirements).bin_file exec_name
-
     requirements = Gem::Requirement.default if
       requirements.empty?
 
@@ -1053,7 +1050,9 @@ An Array (#{env.inspect}) was passed in from #{caller[3]}
   # Find rubygems plugin files in the standard location and load them
 
   def self.load_plugins
-    load_plugin_files Gem::Util.glob_files_in_dir("*#{Gem.plugin_suffix_pattern}", plugindir)
+    Gem.path.each do |gem_path|
+      load_plugin_files Gem::Util.glob_files_in_dir("*#{Gem.plugin_suffix_pattern}", plugindir(gem_path))
+    end
   end
 
   ##
@@ -1112,26 +1111,21 @@ An Array (#{env.inspect}) was passed in from #{caller[3]}
 
     ENV["BUNDLE_GEMFILE"] ||= File.expand_path(path)
     require 'rubygems/user_interaction'
-    Gem::DefaultUserInteraction.use_ui(ui) do
-      require "bundler"
-      begin
-        Bundler.ui.silence do
-          @gemdeps = Bundler.setup
+    require "bundler"
+    begin
+      Gem::DefaultUserInteraction.use_ui(ui) do
+        begin
+          Bundler.ui.silence do
+            @gemdeps = Bundler.setup
+          end
+        ensure
+          Gem::DefaultUserInteraction.ui.close
         end
-      ensure
-        Gem::DefaultUserInteraction.ui.close
       end
-      @gemdeps.requested_specs.map(&:to_spec).sort_by(&:name)
-    end
-
-  rescue => e
-    case e
-    when Gem::LoadError, Gem::UnsatisfiableDependencyError, (defined?(Bundler::GemNotFound) ? Bundler::GemNotFound : Gem::LoadError)
+    rescue Bundler::BundlerError => e
       warn e.message
-      warn "You may need to `gem install -g` to install missing gems"
+      warn "You may need to `bundle install` to install missing gems"
       warn ""
-    else
-      raise
     end
   end
 
@@ -1337,6 +1331,14 @@ begin
 
   require 'rubygems/defaults/operating_system'
 rescue LoadError
+  # Ignored
+rescue StandardError => e
+  msg = "#{e.message}\n" \
+    "Loading the rubygems/defaults/operating_system.rb file caused an error. " \
+    "This file is owned by your OS, not by rubygems upstream. " \
+    "Please find out which OS package this file belongs to and follow the guidelines from your OS to report " \
+    "the problem and ask for help."
+  raise e.class, msg
 end
 
 begin
@@ -1354,5 +1356,3 @@ Gem::Specification.load_defaults
 require 'rubygems/core_ext/kernel_gem'
 require 'rubygems/core_ext/kernel_require'
 require 'rubygems/core_ext/kernel_warn'
-
-Gem.use_gemdeps
diff --git a/lib/rubygems/installer.rb b/lib/rubygems/installer.rb
index 8c286605e1..53c5fc7285 100644
--- a/lib/rubygems/installer.rb
+++ b/lib/rubygems/installer.rb
@@ -761,7 +761,7 @@ class Gem::Installer
 #
 
 require 'rubygems'
-
+#{gemdeps_load(spec.name)}
 version = "#{Gem::Requirement.default_prerelease}"
 
 str = ARGV.first
@@ -782,6 +782,15 @@ end
 TEXT
   end
 
+  def gemdeps_load(name)
+    return '' if name == "bundler"
+
+    <<-TEXT
+
+Gem.use_gemdeps
+TEXT
+  end
+
   ##
   # return the stub script text used to launch the true Ruby script
 
diff --git a/spec/bundler/bundler/cli_spec.rb b/spec/bundler/bundler/cli_spec.rb
index c9dd101f55..c5de12c211 100644
--- a/spec/bundler/bundler/cli_spec.rb
+++ b/spec/bundler/bundler/cli_spec.rb
@@ -111,22 +111,6 @@ RSpec.describe "bundle executable" do
     end
   end
 
-  context "when ENV['RUBYGEMS_GEMDEPS'] is set" do
-    it "displays a warning" do
-      gemfile bundled_app_gemfile, <<-G
-        source "#{file_uri_for(gem_repo1)}"
-        gem 'rack'
-      G
-
-      bundle :install, :env => { "RUBYGEMS_GEMDEPS" => "foo" }
-      expect(err).to include("RUBYGEMS_GEMDEPS")
-      expect(err).to include("conflict with Bundler")
-
-      bundle :install, :env => { "RUBYGEMS_GEMDEPS" => "" }
-      expect(err).not_to include("RUBYGEMS_GEMDEPS")
-    end
-  end
-
   context "with --verbose" do
     it "prints the running command" do
       gemfile "source \"#{file_uri_for(gem_repo1)}\""
diff --git a/spec/bundler/bundler/dsl_spec.rb b/spec/bundler/bundler/dsl_spec.rb
index e6cd43ab59..4d14949c89 100644
--- a/spec/bundler/bundler/dsl_spec.rb
+++ b/spec/bundler/bundler/dsl_spec.rb
@@ -250,7 +250,7 @@ RSpec.describe Bundler::Dsl do
 
         warning = "This Gemfile does not include an explicit global source. " \
           "Not using an explicit global source may result in a different lockfile being generated depending on " \
-          "the gems you have installed locally before bundler is run." \
+          "the gems you have installed locally before bundler is run. " \
           "Instead, define a global source in your Gemfile like this: source \"https://rubygems.org\"."
         expect(Bundler::SharedHelpers).to receive(:major_deprecation).with(2, warning)
 
diff --git a/spec/bundler/commands/binstubs_spec.rb b/spec/bundler/commands/binstubs_spec.rb
index fb5da98bf3..c8eef55266 100644
--- a/spec/bundler/commands/binstubs_spec.rb
+++ b/spec/bundler/commands/binstubs_spec.rb
@@ -287,8 +287,6 @@ RSpec.describe "bundle binstubs <gem>" do
     end
 
     it "sets correct permissions for binstubs" do
-      skip "https://github.com/rubygems/rubygems/issues/3352" if Gem.win_platform?
-
       with_umask(0o002) do
         install_gemfile <<-G
           source "#{file_uri_for(gem_repo1)}"
@@ -297,7 +295,7 @@ RSpec.describe "bundle binstubs <gem>" do
 
         bundle "binstubs rack"
         binary = bundled_app("bin/rackup")
-        expect(File.stat(binary).mode.to_s(8)).to eq("100775")
+        expect(File.stat(binary).mode.to_s(8)).to eq(Gem.win_platform? ? "100644" : "100775")
       end
     end
 
diff --git a/spec/bundler/commands/config_spec.rb b/spec/bundler/commands/config_spec.rb
index 4e13a7903e..48f0ceab78 100644
--- a/spec/bundler/commands/config_spec.rb
+++ b/spec/bundler/commands/config_spec.rb
@@ -88,6 +88,16 @@ RSpec.describe ".bundle/config" do
       bundle "config get path", :env => { "BUNDLE_USER_CONFIG" => bundle_user_config }
       expect(out).to include("Set for the current user (#{bundle_user_config}): \"vendor\"")
     end
+
+    context "when not explicitly configured, but BUNDLE_USER_HOME set" do
+      let(:bundle_user_home) { bundled_app(".bundle").to_s }
+
+      it "uses the right location" do
+        bundle "config set path vendor", :env => { "BUNDLE_USER_HOME" => bundle_user_home }
+        bundle "config get path", :env => { "BUNDLE_USER_HOME" => bundle_user_home }
+        expect(out).to include("Set for the current user (#{bundle_user_home}/config): \"vendor\"")
+      end
+    end
   end
 
   describe "global" do
diff --git a/spec/bundler/commands/exec_spec.rb b/spec/bundler/commands/exec_spec.rb
index 68c4726608..c6648f0a7a 100644
--- a/spec/bundler/commands/exec_spec.rb
+++ b/spec/bundler/commands/exec_spec.rb
@@ -836,7 +836,7 @@ RSpec.describe "bundle exec" do
       let(:exit_code) { Bundler::GemNotFound.new.status_code }
       let(:expected) { "" }
       let(:expected_err) { <<-EOS.strip }
-Could not find gem 'rack (= 2)' in rubygems repository #{file_uri_for(gem_repo1)}/ or installed locally.
+Could not find gem 'rack (= 2)' in locally installed gems.
 The source contains the following versions of 'rack': 0.9.1, 1.0.0
 Run `bundle install` to install missing gems.
       EOS
@@ -863,7 +863,7 @@ Run `bundle install` to install missing gems.
       let(:exit_code) { Bundler::GemNotFound.new.status_code }
       let(:expected) { "" }
       let(:expected_err) { <<-EOS.strip }
-Could not find gem 'rack (= 2)' in rubygems repository #{file_uri_for(gem_repo1)}/ or installed locally.
+Could not find gem 'rack (= 2)' in locally installed gems.
 The source contains the following versions of 'rack': 1.0.0
 Run `bundle install` to install missing gems.
       EOS
diff --git a/spec/bundler/commands/install_spec.rb b/spec/bundler/commands/install_spec.rb
index 412000341f..35c45b68b7 100644
--- a/spec/bundler/commands/install_spec.rb
+++ b/spec/bundler/commands/install_spec.rb
@@ -336,7 +336,7 @@ RSpec.describe "bundle install with gem sources" do
 
       expect(err).to include("This Gemfile does not include an explicit global source. " \
         "Not using an explicit global source may result in a different lockfile being generated depending on " \
-        "the gems you have installed locally before bundler is run." \
+        "the gems you have installed locally before bundler is run. " \
         "Instead, define a global source in your Gemfile like this: source \"https://rubygems.org\".")
     end
 
@@ -759,4 +759,22 @@ RSpec.describe "bundle install with gem sources" do
       )
     end
   end
+
+  context "with --local flag" do
+    before do
+      system_gems "rack-1.0.0", :path => default_bundle_path
+    end
+
+    it "respects installed gems without fetching any remote sources" do
+      install_gemfile <<-G, :local => true
+        source "#{file_uri_for(gem_repo1)}"
+
+        source "https://not-existing-source" do
+          gem "rack"
+        end
+      G
+
+      expect(last_command).to be_success
+    end
+  end
 end
diff --git a/spec/bundler/commands/lock_spec.rb b/spec/bundler/commands/lock_spec.rb
index 21eb6e5456..171ec1ba1d 100644
--- a/spec/bundler/commands/lock_spec.rb
+++ b/spec/bundler/commands/lock_spec.rb
@@ -86,7 +86,7 @@ RSpec.describe "bundle lock" do
   it "does not fetch remote specs when using the --local option" do
     bundle "lock --update --local", :raise_on_error => false
 
-    expect(err).to match(/installed locally/)
+    expect(err).to match(/locally installed gems/)
   end
 
   it "works with --gemfile flag" do
diff --git a/spec/bundler/commands/newgem_spec.rb b/spec/bundler/commands/newgem_spec.rb
index 5cdb3ed5e3..73ae721c69 100644
--- a/spec/bundler/commands/newgem_spec.rb
+++ b/spec/bundler/commands/newgem_spec.rb
@@ -29,36 +29,32 @@ RSpec.describe "bundle gem" do
   end
 
   describe "git repo initialization" do
-    shared_examples_for "a gem with an initial git repo" do
-      before do
-        bundle "gem #{gem_name} #{flags}"
-      end
-
-      it "generates a gem skeleton with a .git folder", :readline do
-        gem_skeleton_assertions
-        expect(bundled_app("#{gem_name}/.git")).to exist
-      end
+    it "generates a gem skeleton with a .git folder", :readline do
+      bundle "gem #{gem_name}"
+      gem_skeleton_assertions
+      expect(bundled_app("#{gem_name}/.git")).to exist
     end
 
-    context "when using the default" do
-      it_behaves_like "a gem with an initial git repo" do
-        let(:flags) { "" }
-      end
+    it "generates a gem skeleton with a .git folder when passing --git", :readline do
+      bundle "gem #{gem_name} --git"
+      gem_skeleton_assertions
+      expect(bundled_app("#{gem_name}/.git")).to exist
     end
 
-    context "when explicitly passing --git" do
-      it_behaves_like "a gem with an initial git repo" do
-        let(:flags) { "--git" }
-      end
+    it "generates a gem skeleton without a .git folder when passing --no-git", :readline do
+      bundle "gem #{gem_name} --no-git"
+      gem_skeleton_assertions
+      expect(bundled_app("#{gem_name}/.git")).not_to exist
     end
 
-    context "when passing --no-git", :readline do
+    context "on a path with spaces" do
       before do
-        bundle "gem #{gem_name} --no-git"
+        Dir.mkdir(bundled_app("path with spaces"))
       end
-      it "generates a gem skeleton without a .git folder" do
-        gem_skeleton_assertions
-        expect(bundled_app("#{gem_name}/.git")).not_to exist
+
+      it "properly initializes git repo", :readline do
+        bundle "gem #{gem_name}", :dir => bundled_app("path with spaces")
+        expect(bundled_app("path with spaces/#{gem_name}/.git")).to exist
       end
     end
   end
@@ -475,6 +471,14 @@ RSpec.describe "bundle gem" do
       expect(bundled_app("#{gem_name}/lib/#{require_path}.rb").read).to match(/class Error < StandardError; end$/)
     end
 
+    it "does not include the gemspec file in files" do
+      bundle "gem #{gem_name}"
+
+      bundler_gemspec = Bundler::GemHelper.new(gemspec_dir).gemspec
+
+      expect(bundler_gemspec.files).not_to include("#{gem_name}.gemspec")
+    end
+
     it "runs rake without problems" do
       bundle "gem #{gem_name}"
 
diff --git a/spec/bundler/commands/post_bundle_message_spec.rb b/spec/bundler/commands/post_bundle_message_spec.rb
index 72f8020b44..3050b87754 100644
--- a/spec/bundler/commands/post_bundle_message_spec.rb
+++ b/spec/bundler/commands/post_bundle_message_spec.rb
@@ -121,7 +121,6 @@ RSpec.describe "post bundle message" do
         G
         expect(err).to include <<-EOS.strip
 Could not find gem 'not-a-gem' in rubygems repository #{file_uri_for(gem_repo1)}/ or installed locally.
-The source does not contain any versions of 'not-a-gem'
         EOS
       end
 
diff --git a/spec/bundler/install/gemfile/sources_spec.rb b/spec/bundler/install/gemfile/sources_spec.rb
index 8c225afb11..9885145662 100644
--- a/spec/bundler/install/gemfile/sources_spec.rb
+++ b/spec/bundler/install/gemfile/sources_spec.rb
@@ -347,7 +347,6 @@ RSpec.describe "bundle install with gems on multiple sources" do
       it "fails" do
         bundle :install, :artifice => "compact_index", :raise_on_error => false
         expect(err).to include("Could not find gem 'private_gem_1' in rubygems repository https://gem.repo2/ or installed locally.")
-        expect(err).to include("The source does not contain any versions of 'private_gem_1'")
       end
     end
 
@@ -1281,7 +1280,7 @@ RSpec.describe "bundle install with gems on multiple sources" do
     expect(out).to include("Using example 0.1.0")
   end
 
-  it "fails inmmediately with a helpful error when a non retriable network error happens while resolving sources" do
+  it "fails inmmediately with a helpful error when a rubygems source does not exist and bundler/setup is required" do
     gemfile <<-G
       source "https://gem.repo1"
 
@@ -1297,6 +1296,21 @@ RSpec.describe "bundle install with gems on multiple sources" do
     end
 
     expect(last_command).to be_failure
+    expect(err).to include("Could not find gem 'example' in locally installed gems.")
+  end
+
+  it "fails inmmediately with a helpful error when a non retriable network error happens while resolving sources" do
+    gemfile <<-G
+      source "https://gem.repo1"
+
+      source "https://gem.repo4" do
+        gem "example"
+      end
+    G
+
+    bundle "install", :artifice => nil, :raise_on_error => false
+
+    expect(last_command).to be_failure
     expect(err).to include("Could not reach host gem.repo4. Check your network connection and try again.")
   end
 
diff --git a/spec/bundler/install/gems/standalone_spec.rb b/spec/bundler/install/gems/standalone_spec.rb
index 6578997cd6..15ffc80e69 100644
--- a/spec/bundler/install/gems/standalone_spec.rb
+++ b/spec/bundler/install/gems/standalone_spec.rb
@@ -147,6 +147,36 @@ RSpec.shared_examples "bundle install --standalone" do
     end
   end
 
+  describe "with Gemfiles using path sources and resulting bundle moved to a folder hierarchy with different nesting" do
+    before do
+      build_lib "minitest", "1.0.0", :path => lib_path("minitest")
+
+      Dir.mkdir bundled_app("app")
+
+      gemfile bundled_app("app/Gemfile"), <<-G
+        source "#{file_uri_for(gem_repo1)}"
+        gem "minitest", :path => "#{lib_path("minitest")}"
+      G
+
+      bundle "install", :standalone => true, :dir => bundled_app("app")
+
+      Dir.mkdir tmp("one_more_level")
+      FileUtils.mv bundled_app, tmp("one_more_level")
+    end
+
+    it "also works" do
+      ruby <<-RUBY, :dir => tmp("one_more_level/bundled_app/app")
+        require "./bundle/bundler/setup"
+
+        require "minitest"
+        puts MINITEST
+      RUBY
+
+      expect(out).to eq("1.0.0")
+      expect(err).to be_empty
+    end
+  end
+
   describe "with gems with native extension", :ruby_repo do
     before do
       bundle "config set --local path #{bundled_app("bundle")}"
@@ -159,7 +189,7 @@ RSpec.shared_examples "bundle install --standalone" do
     it "generates a bundle/bundler/setup.rb with the proper paths" do
       expected_path = bundled_app("bundle/bundler/setup.rb")
       extension_line = File.read(expected_path).each_line.find {|line| line.include? "/extensions/" }.strip
-      expect(extension_line).to start_with '$:.unshift File.expand_path("#{path}/../#{ruby_engine}/#{ruby_version}/extensions/'
+      expect(extension_line).to start_with '$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{RbConfig::CONFIG["ruby_version"]}/extensions/'
       expect(extension_line).to end_with '/very_simple_binary-1.0")'
     end
   end
diff --git a/spec/bundler/other/major_deprecation_spec.rb b/spec/bundler/other/major_deprecation_spec.rb
index 459d777a8b..f97eefeef8 100644
--- a/spec/bundler/other/major_deprecation_spec.rb
+++ b/spec/bundler/other/major_deprecation_spec.rb
@@ -92,6 +92,18 @@ RSpec.describe "major deprecations" do
     end
   end
 
+  describe "bundle exec --no-keep-file-descriptors" do
+    before do
+      bundle "exec --no-keep-file-descriptors -e 1", :raise_on_error => false
+    end
+
+    it "is deprecated", :bundler => "< 3" do
+      expect(deprecations).to include "The `--no-keep-file-descriptors` has been deprecated. `bundle exec` no longer mess with your file descriptors. Close them in the exec'd script if you need to"
+    end
+
+    pending "is removed and shows a helpful error message about it", :bundler => "3"
+  end
+
   describe "bundle update --quiet" do
     it "does not print any deprecations" do
       bundle :update, :quiet => true, :raise_on_error => false
diff --git a/spec/bundler/spec_helper.rb b/spec/bundler/spec_helper.rb
index 80b0ccff4d..4d558b9907 100644
--- a/spec/bundler/spec_helper.rb
+++ b/spec/bundler/spec_helper.rb
@@ -73,6 +73,7 @@ RSpec.configure do |config|
     Spec::Rubygems.test_setup
     ENV["BUNDLE_SPEC_RUN"] = "true"
     ENV["BUNDLE_USER_CONFIG"] = ENV["BUNDLE_USER_CACHE"] = ENV["BUNDLE_USER_PLUGIN"] = nil
+    ENV["RUBYGEMS_GEMDEPS"] = nil
     ENV["XDG_CONFIG_HOME"] = nil
     ENV["GEMRC"] = nil
 
diff --git a/spec/bundler/support/indexes.rb b/spec/bundler/support/indexes.rb
index bf4300edb2..91dd699b5f 100644
--- a/spec/bundler/support/indexes.rb
+++ b/spec/bundler/support/indexes.rb
@@ -17,7 +17,7 @@ module Spec
     def resolve(args = [])
       @platforms ||= ["ruby"]
       deps = []
-      default_source = instance_double("Bundler::Source::Rubygems", :specs => @index)
+      default_source = instance_double("Bundler::Source::Rubygems", :specs => @index, :to_err => "locally install gems")
       source_requirements = { :default => default_source }
       @deps.each do |d|
         source_requirements[d.name] = d.source = default_source
diff --git a/test/rubygems/helper.rb b/test/rubygems/helper.rb
index c3befb535f..fd2763db41 100644
--- a/test/rubygems/helper.rb
+++ b/test/rubygems/helper.rb
@@ -1297,7 +1297,11 @@ Also, a list:
   end
 
   def ruby_with_rubygems_in_load_path
-    [Gem.ruby, "-I", File.expand_path("../../lib", __dir__)]
+    [Gem.ruby, "-I", rubygems_path]
+  end
+
+  def rubygems_path
+    $LOAD_PATH.find{|p| p == File.dirname($LOADED_FEATURES.find{|f| f.end_with?("/rubygems.rb") }) }
   end
 
   def with_clean_path_to_ruby
diff --git a/test/rubygems/test_gem.rb b/test/rubygems/test_gem.rb
index 79ea89e2fa..da154dac75 100644
--- a/test/rubygems/test_gem.rb
+++ b/test/rubygems/test_gem.rb
@@ -19,7 +19,6 @@ class TestGem < Gem::TestCase
 
     common_installer_setup
 
-    ENV.delete 'RUBYGEMS_GEMDEPS'
     @additional = %w[a b].map {|d| File.join @tempdir, d }
 
     util_remove_interrupt_command
@@ -540,7 +539,6 @@ class TestGem < Gem::TestCase
       s.executables = []
     end
     install_specs spec
-    # Should not find a-10's non-abin (bug)
     assert_equal @abin_path, Gem.bin_path('a', 'abin')
   end
 
@@ -664,22 +662,22 @@ class TestGem < Gem::TestCase
   end
 
   def test_self_use_gemdeps
-    rubygems_gemdeps, ENV['RUBYGEMS_GEMDEPS'] = ENV['RUBYGEMS_GEMDEPS'], '-'
+    with_rubygems_gemdeps('-') do
+      FileUtils.mkdir_p 'detect/a/b'
+      FileUtils.mkdir_p 'detect/a/Isolate'
 
-    FileUtils.mkdir_p 'detect/a/b'
-    FileUtils.mkdir_p 'detect/a/Isolate'
+      FileUtils.touch 'detect/Isolate'
 
-    FileUtils.touch 'detect/Isolate'
+      begin
+        Dir.chdir 'detect/a/b'
 
-    begin
-      Dir.chdir 'detect/a/b'
+        Gem.use_gemdeps
 
-      assert_equal add_bundler_full_name([]), Gem.use_gemdeps.map(&:full_name)
-    ensure
-      Dir.chdir @tempdir
+        assert_equal add_bundler_full_name([]), loaded_spec_names
+      ensure
+        Dir.chdir @tempdir
+      end
     end
-  ensure
-    ENV['RUBYGEMS_GEMDEPS'] = rubygems_gemdeps
   end
 
   def test_self_dir
@@ -1580,6 +1578,31 @@ class TestGem < Gem::TestCase
     assert_equal %w[plugin], PLUGINS_LOADED
   end
 
+  def test_load_user_installed_plugins
+    plugin_path = File.join "lib", "rubygems_plugin.rb"
+
+    Dir.chdir @tempdir do
+      FileUtils.mkdir_p 'lib'
+      File.open plugin_path, "w" do |fp|
+        fp.puts "class TestGem; PLUGINS_LOADED << 'plugin'; end"
+      end
+
+      foo = util_spec 'foo', '1' do |s|
+        s.files << plugin_path
+      end
+
+      install_gem_user foo
+    end
+
+    Gem.paths = { "GEM_PATH" => [Gem.dir, Gem.user_dir].join(File::PATH_SEPARATOR) }
+
+    gem 'foo'
+
+    Gem.load_plugins
+
+    assert_equal %w[plugin], PLUGINS_LOADED
+  end
+
   def test_load_env_plugins
     with_plugin('load') { Gem.load_env_plugins }
     assert_equal :loaded, TEST_PLUGIN_LOAD rescue nil
@@ -1689,11 +1712,11 @@ class TestGem < Gem::TestCase
       f.puts "gem 'c'"
     end
 
-    ENV['RUBYGEMS_GEMDEPS'] = path
-
-    Gem.use_gemdeps
+    with_rubygems_gemdeps(path) do
+      Gem.use_gemdeps
 
-    assert_equal add_bundler_full_name(%W[a-1 b-1 c-1]), loaded_spec_names
+      assert_equal add_bundler_full_name(%W[a-1 b-1 c-1]), loaded_spec_names
+    end
   end
 
   def test_auto_activation_of_used_gemdeps_file
@@ -1711,10 +1734,13 @@ class TestGem < Gem::TestCase
       f.puts "gem 'c'"
     end
 
-    ENV['RUBYGEMS_GEMDEPS'] = "-"
+    with_rubygems_gemdeps("-") do
+      expected_specs = [a, b, util_spec("bundler", Bundler::VERSION), c].compact.map(&:full_name)
+
+      Gem.use_gemdeps
 
-    expected_specs = [a, b, util_spec("bundler", Bundler::VERSION), c].compact
-    assert_equal expected_specs, Gem.use_gemdeps.sort_by {|s| s.name }
+      assert_equal expected_specs, loaded_spec_names
+    end
   end
 
   BUNDLER_LIB_PATH = File.expand_path $LOAD_PATH.find {|lp| File.file?(File.join(lp, "bundler.rb")) }
@@ -1726,10 +1752,18 @@ class TestGem < Gem::TestCase
     names
   end
 
-  def test_looks_for_gemdeps_files_automatically_on_start
+  def test_looks_for_gemdeps_files_automatically_from_binstubs
     pend "Requiring bundler messes things up" if Gem.java_platform?
 
-    a = util_spec "a", "1", nil, "lib/a.rb"
+    a = util_spec "a", "1" do |s|
+      s.executables = %w[foo]
+      s.bindir = "exe"
+    end
+
+    write_file File.join(@tempdir, 'exe', 'foo') do |fp|
+      fp.puts "puts Gem.loaded_specs.values.map(&:full_name).sort"
+    end
+
     b = util_spec "b", "1", nil, "lib/b.rb"
     c = util_spec "c", "1", nil, "lib/c.rb"
 
@@ -1741,31 +1775,44 @@ class TestGem < Gem::TestCase
     install_gem c, :install_dir => path
 
     ENV['GEM_PATH'] = path
-    ENV['RUBYGEMS_GEMDEPS'] = "-"
 
-    path = File.join @tempdir, "gem.deps.rb"
-    cmd = [*ruby_with_rubygems_in_load_path,
-           "-I#{BUNDLER_LIB_PATH}"]
-    cmd << "-eputs Gem.loaded_specs.values.map(&:full_name).sort"
+    with_rubygems_gemdeps("-") do
+      new_PATH = [File.join(path, "bin"), ENV["PATH"]].join(File::PATH_SEPARATOR)
+      new_RUBYOPT = "-I#{rubygems_path} -I#{BUNDLER_LIB_PATH}"
 
-    File.open path, "w" do |f|
-      f.puts "gem 'a'"
-    end
-    out0 = IO.popen(cmd, &:read).split(/\n/)
+      path = File.join @tempdir, "gem.deps.rb"
 
-    File.open path, "a" do |f|
-      f.puts "gem 'b'"
-      f.puts "gem 'c'"
-    end
-    out = IO.popen(cmd, &:read).split(/\n/)
+      File.open path, "w" do |f|
+        f.puts "gem 'a'"
+      end
+      out0 = with_path_and_rubyopt(new_PATH, new_RUBYOPT) do
+        IO.popen("foo", &:read).split(/\n/)
+      end
+
+      File.open path, "a" do |f|
+        f.puts "gem 'b'"
+        f.puts "gem 'c'"
+      end
+      out = with_path_and_rubyopt(new_PATH, new_RUBYOPT) do
+        IO.popen("foo", &:read).split(/\n/)
+      end
 
-    assert_equal ["b-1", "c-1"], out - out0
+      assert_equal ["b-1", "c-1"], out - out0
+    end
   end
 
-  def test_looks_for_gemdeps_files_automatically_on_start_in_parent_dir
+  def test_looks_for_gemdeps_files_automatically_from_binstubs_in_parent_dir
     pend "Requiring bundler messes things up" if Gem.java_platform?
 
-    a = util_spec "a", "1", nil, "lib/a.rb"
+    a = util_spec "a", "1" do |s|
+      s.executables = %w[foo]
+      s.bindir = "exe"
+    end
+
+    write_file File.join(@tempdir, 'exe', 'foo') do |fp|
+      fp.puts "puts Gem.loaded_specs.values.map(&:full_name).sort"
+    end
+
     b = util_spec "b", "1", nil, "lib/b.rb"
     c = util_spec "c", "1", nil, "lib/c.rb"
 
@@ -1777,29 +1824,34 @@ class TestGem < Gem::TestCase
     install_gem c, :install_dir => path
 
     ENV['GEM_PATH'] = path
-    ENV['RUBYGEMS_GEMDEPS'] = "-"
 
-    Dir.mkdir "sub1"
+    with_rubygems_gemdeps("-") do
+      Dir.mkdir "sub1"
 
-    path = File.join @tempdir, "gem.deps.rb"
-    cmd = [*ruby_with_rubygems_in_load_path, "-Csub1",
-           "-I#{BUNDLER_LIB_PATH}"]
-    cmd << "-eputs Gem.loaded_specs.values.map(&:full_name).sort"
+      new_PATH = [File.join(path, "bin"), ENV["PATH"]].join(File::PATH_SEPARATOR)
+      new_RUBYOPT = "-I#{rubygems_path} -I#{BUNDLER_LIB_PATH}"
 
-    File.open path, "w" do |f|
-      f.puts "gem 'a'"
-    end
-    out0 = IO.popen(cmd, &:read).split(/\n/)
+      path = File.join @tempdir, "gem.deps.rb"
 
-    File.open path, "a" do |f|
-      f.puts "gem 'b'"
-      f.puts "gem 'c'"
-    end
-    out = IO.popen(cmd, &:read).split(/\n/)
+      File.open path, "w" do |f|
+        f.puts "gem 'a'"
+      end
+      out0 = with_path_and_rubyopt(new_PATH, new_RUBYOPT) do
+        IO.popen("foo", :chdir => "sub1", &:read).split(/\n/)
+      end
+
+      File.open path, "a" do |f|
+        f.puts "gem 'b'"
+        f.puts "gem 'c'"
+      end
+      out = with_path_and_rubyopt(new_PATH, new_RUBYOPT) do
+        IO.popen("foo", :chdir => "sub1", &:read).split(/\n/)
+      end
 
-    Dir.rmdir "sub1"
+      Dir.rmdir "sub1"
 
-    assert_equal ["b-1", "c-1"], out - out0
+      assert_equal ["b-1", "c-1"], out - out0
+    end
   end
 
   def test_register_default_spec
@@ -1863,21 +1915,19 @@ class TestGem < Gem::TestCase
   end
 
   def test_use_gemdeps_ENV
-    rubygems_gemdeps, ENV['RUBYGEMS_GEMDEPS'] = ENV['RUBYGEMS_GEMDEPS'], nil
-
-    spec = util_spec 'a', 1
+    with_rubygems_gemdeps(nil) do
+      spec = util_spec 'a', 1
 
-    refute spec.activated?
+      refute spec.activated?
 
-    File.open 'gem.deps.rb', 'w' do |io|
-      io.write 'gem "a"'
-    end
+      File.open 'gem.deps.rb', 'w' do |io|
+        io.write 'gem "a"'
+      end
 
-    Gem.use_gemdeps
+      Gem.use_gemdeps
 
-    refute spec.activated?
-  ensure
-    ENV['RUBYGEMS_GEMDEPS'] = rubygems_gemdeps
+      refute spec.activated?
+    end
   end
 
   def test_use_gemdeps_argument_missing
@@ -1890,110 +1940,96 @@ class TestGem < Gem::TestCase
   end
 
   def test_use_gemdeps_argument_missing_match_ENV
-    rubygems_gemdeps, ENV['RUBYGEMS_GEMDEPS'] =
-      ENV['RUBYGEMS_GEMDEPS'], 'gem.deps.rb'
+    with_rubygems_gemdeps('gem.deps.rb') do
+      e = assert_raise ArgumentError do
+        Gem.use_gemdeps 'gem.deps.rb'
+      end
 
-    e = assert_raise ArgumentError do
-      Gem.use_gemdeps 'gem.deps.rb'
+      assert_equal 'Unable to find gem dependencies file at gem.deps.rb',
+                   e.message
     end
-
-    assert_equal 'Unable to find gem dependencies file at gem.deps.rb',
-                 e.message
-  ensure
-    ENV['RUBYGEMS_GEMDEPS'] = rubygems_gemdeps
   end
 
   def test_use_gemdeps_automatic
-    rubygems_gemdeps, ENV['RUBYGEMS_GEMDEPS'] = ENV['RUBYGEMS_GEMDEPS'], '-'
-
-    spec = util_spec 'a', 1
-    install_specs spec
-    spec = Gem::Specification.find {|s| s == spec }
+    with_rubygems_gemdeps('-') do
+      spec = util_spec 'a', 1
+      install_specs spec
+      spec = Gem::Specification.find {|s| s == spec }
 
-    refute spec.activated?
+      refute spec.activated?
 
-    File.open 'Gemfile', 'w' do |io|
-      io.write 'gem "a"'
-    end
+      File.open 'Gemfile', 'w' do |io|
+        io.write 'gem "a"'
+      end
 
-    Gem.use_gemdeps
+      Gem.use_gemdeps
 
-    assert_equal add_bundler_full_name(%W[a-1]), loaded_spec_names
-  ensure
-    ENV['RUBYGEMS_GEMDEPS'] = rubygems_gemdeps
+      assert_equal add_bundler_full_name(%W[a-1]), loaded_spec_names
+    end
   end
 
   def test_use_gemdeps_automatic_missing
-    rubygems_gemdeps, ENV['RUBYGEMS_GEMDEPS'] = ENV['RUBYGEMS_GEMDEPS'], '-'
+    with_rubygems_gemdeps('-') do
+      Gem.use_gemdeps
 
-    Gem.use_gemdeps
-
-    assert true # count
-  ensure
-    ENV['RUBYGEMS_GEMDEPS'] = rubygems_gemdeps
+      assert true # count
+    end
   end
 
   def test_use_gemdeps_disabled
-    rubygems_gemdeps, ENV['RUBYGEMS_GEMDEPS'] = ENV['RUBYGEMS_GEMDEPS'], ''
+    with_rubygems_gemdeps('') do
+      spec = util_spec 'a', 1
 
-    spec = util_spec 'a', 1
+      refute spec.activated?
 
-    refute spec.activated?
-
-    File.open 'gem.deps.rb', 'w' do |io|
-      io.write 'gem "a"'
-    end
+      File.open 'gem.deps.rb', 'w' do |io|
+        io.write 'gem "a"'
+      end
 
-    Gem.use_gemdeps
+      Gem.use_gemdeps
 
-    refute spec.activated?
-  ensure
-    ENV['RUBYGEMS_GEMDEPS'] = rubygems_gemdeps
+      refute spec.activated?
+    end
   end
 
   def test_use_gemdeps_missing_gem
-    rubygems_gemdeps, ENV['RUBYGEMS_GEMDEPS'] = ENV['RUBYGEMS_GEMDEPS'], 'x'
-
-    File.open 'x', 'w' do |io|
-      io.write 'gem "a"'
-    end
+    with_rubygems_gemdeps('x') do
+      File.open 'x', 'w' do |io|
+        io.write 'gem "a"'
+      end
 
-    expected = <<-EXPECTED
+      expected = <<-EXPECTED
 Could not find gem 'a' in locally installed gems.
-The source does not contain any versions of 'a'
-You may need to `gem install -g` to install missing gems
+You may need to `bundle install` to install missing gems
 
-    EXPECTED
+      EXPECTED
 
-    Gem::Deprecate.skip_during do
-      actual_stdout, actual_stderr = capture_output do
-        Gem.use_gemdeps
+      Gem::Deprecate.skip_during do
+        actual_stdout, actual_stderr = capture_output do
+          Gem.use_gemdeps
+        end
+        assert_empty actual_stdout
+        assert_equal(expected, actual_stderr)
       end
-      assert_empty actual_stdout
-      assert_equal(expected, actual_stderr)
     end
-  ensure
-    ENV['RUBYGEMS_GEMDEPS'] = rubygems_gemdeps
   end
 
   def test_use_gemdeps_specific
-    rubygems_gemdeps, ENV['RUBYGEMS_GEMDEPS'] = ENV['RUBYGEMS_GEMDEPS'], 'x'
+    with_rubygems_gemdeps('x') do
+      spec = util_spec 'a', 1
+      install_specs spec
 
-    spec = util_spec 'a', 1
-    install_specs spec
-
-    spec = Gem::Specification.find {|s| s == spec }
-    refute spec.activated?
+      spec = Gem::Specification.find {|s| s == spec }
+      refute spec.activated?
 
-    File.open 'x', 'w' do |io|
-      io.write 'gem "a"'
-    end
+      File.open 'x', 'w' do |io|
+        io.write 'gem "a"'
+      end
 
-    Gem.use_gemdeps
+      Gem.use_gemdeps
 
-    assert_equal add_bundler_full_name(%W[a-1]), loaded_spec_names
-  ensure
-    ENV['RUBYGEMS_GEMDEPS'] = rubygems_gemdeps
+      assert_equal add_bundler_full_name(%W[a-1]), loaded_spec_names
+    end
   end
 
   def test_operating_system_defaults
@@ -2111,4 +2147,22 @@ You may need to `gem install -g` to install missing gems
   def util_cache_dir
     File.join Gem.dir, "cache"
   end
+
+  def with_path_and_rubyopt(path_value, rubyopt_value)
+    path, ENV['PATH'] = ENV['PATH'], path_value
+    rubyopt, ENV['RUBYOPT'] = ENV['RUBYOPT'], rubyopt_value
+
+    yield
+  ensure
+    ENV['PATH'] = path
+    ENV['RUBYOPT'] = rubyopt
+  end
+
+  def with_rubygems_gemdeps(value)
+    rubygems_gemdeps, ENV['RUBYGEMS_GEMDEPS'] = ENV['RUBYGEMS_GEMDEPS'], value
+
+    yield
+  ensure
+    ENV['RUBYGEMS_GEMDEPS'] = rubygems_gemdeps
+  end
 end
diff --git a/test/rubygems/test_gem_installer.rb b/test/rubygems/test_gem_installer.rb
index a2b390d639..988f14146d 100644
--- a/test/rubygems/test_gem_installer.rb
+++ b/test/rubygems/test_gem_installer.rb
@@ -33,6 +33,8 @@ class TestGemInstaller < Gem::InstallerTestCase
 
 require 'rubygems'
 
+Gem.use_gemdeps
+
 version = \">= 0.a\"
 
 str = ARGV.first
diff --git a/test/rubygems/test_rubygems.rb b/test/rubygems/test_rubygems.rb
new file mode 100644
index 0000000000..493b9fdf4a
--- /dev/null
+++ b/test/rubygems/test_rubygems.rb
@@ -0,0 +1,44 @@
+require_relative 'helper'
+
+class GemTest < Gem::TestCase
+  def test_rubygems_normal_behaviour
+    _ = Gem::Util.popen(*ruby_with_rubygems_in_load_path, '-e', "'require \"rubygems\"'", {:err => [:child, :out]}).strip
+    assert $?.success?
+  end
+
+  def test_operating_system_other_exceptions
+    pend "does not apply to truffleruby" if RUBY_ENGINE == 'truffleruby'
+
+    path = util_install_operating_system_rb <<-RUBY
+      intentionally_not_implemented_method
+    RUBY
+
+    output = Gem::Util.popen(*ruby_with_rubygems_and_fake_operating_system_in_load_path(path), '-e', "'require \"rubygems\"'", {:err => [:child, :out]}).strip
+    assert !$?.success?
+    assert_includes output, "undefined local variable or method `intentionally_not_implemented_method'"
+    assert_includes output, "Loading the rubygems/defaults/operating_system.rb file caused an error. " \
+    "This file is owned by your OS, not by rubygems upstream. " \
+    "Please find out which OS package this file belongs to and follow the guidelines from your OS to report " \
+    "the problem and ask for help."
+  end
+
+  private
+
+  def util_install_operating_system_rb(content)
+    dir_lib = Dir.mktmpdir("test_operating_system_lib", @tempdir)
+    dir_lib_arg = File.join dir_lib
+
+    dir_lib_rubygems_defaults_arg = File.join dir_lib_arg, "lib", "rubygems", "defaults"
+    FileUtils.mkdir_p dir_lib_rubygems_defaults_arg
+
+    operating_system_rb = File.join dir_lib_rubygems_defaults_arg, "operating_system.rb"
+
+    File.open(operating_system_rb, 'w') {|f| f.write content }
+
+    File.join dir_lib_arg, "lib"
+  end
+
+  def ruby_with_rubygems_and_fake_operating_system_in_load_path(operating_system_path)
+    [Gem.ruby, "-I", operating_system_path, "-I" , $LOAD_PATH.find{|p| p == File.dirname($LOADED_FEATURES.find{|f| f.end_with?("/rubygems.rb") }) }]
+  end
+end
diff --git a/tool/bundler/rubocop_gems.rb.lock b/tool/bundler/rubocop_gems.rb.lock
index 45a33136bb..c95c6f15f5 100644
--- a/tool/bundler/rubocop_gems.rb.lock
+++ b/tool/bundler/rubocop_gems.rb.lock
@@ -57,4 +57,4 @@ DEPENDENCIES
   test-unit
 
 BUNDLED WITH
-   2.2.25
+   2.2.26
diff --git a/tool/bundler/test_gems.rb.lock b/tool/bundler/test_gems.rb.lock
index ae002ef2e4..f51d8a4b66 100644
--- a/tool/bundler/test_gems.rb.lock
+++ b/tool/bundler/test_gems.rb.lock
@@ -40,4 +40,4 @@ DEPENDENCIES
   webrick (= 1.7.0)
 
 BUNDLED WITH
-   2.2.25
+   2.2.26