Merge RubyGems-3.3.15 and Bundler-2.3.15

40 files changed, 385 insertions, 100 deletions

diff --git a/lib/bundler.rb b/lib/bundler.rb
index 0be01d1808..c99114ae64 100644
--- a/lib/bundler.rb
+++ b/lib/bundler.rb
@@ -97,6 +97,17 @@ module Bundler
       @bundle_path ||= Pathname.new(configured_bundle_path.path).expand_path(root)
     end
 
+    def create_bundle_path
+      SharedHelpers.filesystem_access(bundle_path.to_s) do |p|
+        mkdir_p(p)
+      end unless bundle_path.exist?
+
+      @bundle_path = bundle_path.realpath
+    rescue Errno::EEXIST
+      raise PathError, "Could not install to path `#{bundle_path}` " \
+        "because a file already exists at that path. Either remove or rename the file so the directory can be created."
+    end
+
     def configured_bundle_path
       @configured_bundle_path ||= settings.path.tap(&:validate!)
     end
diff --git a/lib/bundler/dsl.rb b/lib/bundler/dsl.rb
index 8983ef3e2b..1ae19a46e9 100644
--- a/lib/bundler/dsl.rb
+++ b/lib/bundler/dsl.rb
@@ -124,19 +124,17 @@ module Bundler
             raise GemfileError, "You cannot specify the same gem twice with different version requirements.\n" \
                             "You specified: #{current.name} (#{current.requirement}) and #{dep.name} (#{dep.requirement})" \
                              "#{update_prompt}"
+          elsif current.source != dep.source
+            return if dep.type == :development
+            raise GemfileError, "You cannot specify the same gem twice coming from different sources.\n" \
+                            "You specified that #{dep.name} (#{dep.requirement}) should come from " \
+                            "#{current.source || "an unspecified source"} and #{dep.source}\n"
           else
             Bundler.ui.warn "Your Gemfile lists the gem #{current.name} (#{current.requirement}) more than once.\n" \
                             "You should probably keep only one of them.\n" \
                             "Remove any duplicate entries and specify the gem only once.\n" \
                             "While it's not a problem now, it could cause errors if you change the version of one of them later."
           end
-
-          if current.source != dep.source
-            return if dep.type == :development
-            raise GemfileError, "You cannot specify the same gem twice coming from different sources.\n" \
-                            "You specified that #{dep.name} (#{dep.requirement}) should come from " \
-                            "#{current.source || "an unspecified source"} and #{dep.source}\n"
-          end
         end
       end
 
diff --git a/lib/bundler/errors.rb b/lib/bundler/errors.rb
index 9ad7460e58..0bc1a860df 100644
--- a/lib/bundler/errors.rb
+++ b/lib/bundler/errors.rb
@@ -79,10 +79,6 @@ module Bundler
       case @permission_type
       when :create
         "executable permissions for all parent directories and write permissions for `#{parent_folder}`"
-      when :delete
-        permissions = "executable permissions for all parent directories and write permissions for `#{parent_folder}`"
-        permissions += ", and the same thing for all subdirectories inside #{@path}" if File.directory?(@path)
-        permissions
       else
         "#{@permission_type} permissions for that path"
       end
@@ -172,4 +168,16 @@ module Bundler
 
     status_code(32)
   end
+
+  class DirectoryRemovalError < BundlerError
+    def initialize(orig_exception, msg)
+      full_message = "#{msg}.\n" \
+                     "The underlying error was #{orig_exception.class}: #{orig_exception.message}, with backtrace:\n" \
+                     "  #{orig_exception.backtrace.join("\n  ")}\n\n" \
+                     "Bundler Error Backtrace:"
+      super(full_message)
+    end
+
+    status_code(36)
+  end
 end
diff --git a/lib/bundler/friendly_errors.rb b/lib/bundler/friendly_errors.rb
index cc615db60c..ff6cdc4123 100644
--- a/lib/bundler/friendly_errors.rb
+++ b/lib/bundler/friendly_errors.rb
@@ -65,8 +65,7 @@ module Bundler
         --- ERROR REPORT TEMPLATE -------------------------------------------------------
 
         ```
-        #{e.class}: #{e.message}
-          #{e.backtrace && e.backtrace.join("\n          ").chomp}
+        #{exception_message(e)}
         ```
 
         #{Bundler::Env.report}
@@ -85,6 +84,21 @@ module Bundler
       EOS
     end
 
+    def exception_message(error)
+      message = serialized_exception_for(error)
+      cause = error.cause
+      return message unless cause
+
+      message + serialized_exception_for(cause)
+    end
+
+    def serialized_exception_for(e)
+      <<-EOS.gsub(/^ {8}/, "")
+        #{e.class}: #{e.message}
+          #{e.backtrace && e.backtrace.join("\n          ").chomp}
+      EOS
+    end
+
     def issues_url(exception)
       message = exception.message.lines.first.tr(":", " ").chomp
       message = message.split("-").first if exception.is_a?(Errno)
diff --git a/lib/bundler/injector.rb b/lib/bundler/injector.rb
index 42f837a919..f6550abe88 100644
--- a/lib/bundler/injector.rb
+++ b/lib/bundler/injector.rb
@@ -72,6 +72,10 @@ module Bundler
 
         deps.each {|dep| Bundler.ui.confirm "#{SharedHelpers.pretty_dependency(dep, false)} was removed." }
       end
+
+      # Invalidate the cached Bundler.definition.
+      # This prevents e.g. `bundle remove ...` from using outdated information.
+      Bundler.reset_paths!
     end
 
     private
diff --git a/lib/bundler/inline.rb b/lib/bundler/inline.rb
index a718418fce..8ef580f1f0 100644
--- a/lib/bundler/inline.rb
+++ b/lib/bundler/inline.rb
@@ -38,12 +38,7 @@ def gemfile(install = false, options = {}, &gemfile)
   raise ArgumentError, "Unknown options: #{opts.keys.join(", ")}" unless opts.empty?
 
   begin
-    old_root = Bundler.method(:root)
-    bundler_module = class << Bundler; self; end
-    bundler_module.send(:remove_method, :root)
-    def Bundler.root
-      Bundler::SharedHelpers.pwd.expand_path
-    end
+    Bundler.instance_variable_set(:@bundle_path, Pathname.new(Gem.dir))
     old_gemfile = ENV["BUNDLE_GEMFILE"]
     Bundler::SharedHelpers.set_env "BUNDLE_GEMFILE", "Gemfile"
 
@@ -71,11 +66,6 @@ def gemfile(install = false, options = {}, &gemfile)
       runtime.setup.require
     end
   ensure
-    if bundler_module
-      bundler_module.send(:remove_method, :root)
-      bundler_module.send(:define_method, :root, old_root)
-    end
-
     if old_gemfile
       ENV["BUNDLE_GEMFILE"] = old_gemfile
     else
diff --git a/lib/bundler/installer.rb b/lib/bundler/installer.rb
index 915a04c0dc..f195d36600 100644
--- a/lib/bundler/installer.rb
+++ b/lib/bundler/installer.rb
@@ -66,7 +66,7 @@ module Bundler
     # require paths and save them in a `setup.rb` file. See `bundle standalone --help` for more
     # information.
     def run(options)
-      create_bundle_path
+      Bundler.create_bundle_path
 
       ProcessLock.lock do
         if Bundler.frozen_bundle?
@@ -262,15 +262,6 @@ module Bundler
       end
     end
 
-    def create_bundle_path
-      SharedHelpers.filesystem_access(Bundler.bundle_path.to_s) do |p|
-        Bundler.mkdir_p(p)
-      end unless Bundler.bundle_path.exist?
-    rescue Errno::EEXIST
-      raise PathError, "Could not install to path `#{Bundler.bundle_path}` " \
-        "because a file already exists at that path. Either remove or rename the file so the directory can be created."
-    end
-
     # returns whether or not a re-resolve was needed
     def resolve_if_needed(options)
       if !@definition.unlocking? && !options["force"] && !Bundler.settings[:inline] && Bundler.default_lockfile.file?
diff --git a/lib/bundler/process_lock.rb b/lib/bundler/process_lock.rb
index a5cc614e20..0297f80e2c 100644
--- a/lib/bundler/process_lock.rb
+++ b/lib/bundler/process_lock.rb
@@ -12,7 +12,7 @@ module Bundler
         yield
         f.flock(File::LOCK_UN)
       end
-    rescue Errno::EACCES, Errno::ENOLCK, Errno::ENOTSUP
+    rescue Errno::EACCES, Errno::ENOLCK, Errno::ENOTSUP, Errno::EPERM, Errno::EROFS
       # In the case the user does not have access to
       # create the lock file or is using NFS where
       # locks are not available we skip locking.
diff --git a/lib/bundler/resolver.rb b/lib/bundler/resolver.rb
index 2285114c57..d749694952 100644
--- a/lib/bundler/resolver.rb
+++ b/lib/bundler/resolver.rb
@@ -19,13 +19,15 @@ module Bundler
     #   collection of gemspecs is returned. Otherwise, nil is returned.
     def self.resolve(requirements, source_requirements = {}, base = [], gem_version_promoter = GemVersionPromoter.new, additional_base_requirements = [], platforms = nil)
       base = SpecSet.new(base) unless base.is_a?(SpecSet)
-      resolver = new(source_requirements, base, gem_version_promoter, additional_base_requirements, platforms)
+      metadata_requirements, regular_requirements = requirements.partition {|dep| dep.name.end_with?("\0") }
+      resolver = new(source_requirements, base, gem_version_promoter, additional_base_requirements, platforms, metadata_requirements)
       result = resolver.start(requirements)
-      SpecSet.new(SpecSet.new(result).for(requirements.reject {|dep| dep.name.end_with?("\0") }))
+      SpecSet.new(SpecSet.new(result).for(regular_requirements))
     end
 
-    def initialize(source_requirements, base, gem_version_promoter, additional_base_requirements, platforms)
+    def initialize(source_requirements, base, gem_version_promoter, additional_base_requirements, platforms, metadata_requirements)
       @source_requirements = source_requirements
+      @metadata_requirements = metadata_requirements
       @base = base
       @resolver = Molinillo::Resolver.new(self, self)
       @search_for = {}
@@ -344,8 +346,6 @@ module Bundler
             trees.sort_by! {|t| t.reverse.map(&:name) }
           end
 
-          metadata_requirements = {}
-
           o << trees.map do |tree|
             t = "".dup
             depth = 2
@@ -354,7 +354,6 @@ module Bundler
             base_tree_name = base_tree.name
 
             if base_tree_name.end_with?("\0")
-              metadata_requirements[base_tree_name] = base_tree
               t = nil
             else
               tree.each do |req|
@@ -393,10 +392,10 @@ module Bundler
               end
             end
           elsif name.end_with?("\0")
-            o << %(\n  Current #{name} version:\n    #{SharedHelpers.pretty_dependency(metadata_requirements[name])}\n\n)
+            o << %(\n  Current #{name} version:\n    #{SharedHelpers.pretty_dependency(@metadata_requirements.find {|req| req.name == name })}\n\n)
           elsif conflict.locked_requirement
             o << "\n"
-            o << %(Running `bundle update` will rebuild your snapshot from scratch, using only\n)
+            o << %(Deleting your #{name_for_locking_dependency_source} file and running `bundle install` will rebuild your snapshot from scratch, using only\n)
             o << %(the gems in your Gemfile, which may resolve the conflict.\n)
           elsif !conflict.existing
             o << "\n"
diff --git a/lib/bundler/rubygems_gem_installer.rb b/lib/bundler/rubygems_gem_installer.rb
index 452583617b..87b9772c27 100644
--- a/lib/bundler/rubygems_gem_installer.rb
+++ b/lib/bundler/rubygems_gem_installer.rb
@@ -93,14 +93,9 @@ module Bundler
     private
 
     def strict_rm_rf(dir)
-      # FileUtils.rm_rf should probably rise in case of permission issues like
-      # `rm -rf` does. However, it fails to delete the folder silently due to
-      # https://github.com/ruby/fileutils/issues/57. It should probably be fixed
-      # inside `fileutils` but for now I`m checking whether the folder was
-      # removed after it completes, and raising otherwise.
-      FileUtils.rm_rf dir
-
-      raise PermissionError.new(dir, :delete) if File.directory?(dir)
+      Bundler.rm_rf dir
+    rescue Errno::ENOTEMPTY => e
+      raise DirectoryRemovalError.new(e.cause, "Could not delete previous installation of `#{dir}`")
     end
 
     def validate_bundler_checksum(checksum)
diff --git a/lib/bundler/settings.rb b/lib/bundler/settings.rb
index 8f263cd012..398c66055a 100644
--- a/lib/bundler/settings.rb
+++ b/lib/bundler/settings.rb
@@ -487,7 +487,7 @@ module Bundler
       /ix.freeze
 
     def self.key_for(key)
-      key = normalize_uri(key).to_s if key.is_a?(String) && /https?:/ =~ key
+      key = normalize_uri(key).to_s if key.is_a?(String) && key.start_with?("http", "mirror.http")
       key = key.to_s.gsub(".", "__").gsub("-", "___").upcase
       "BUNDLE_#{key}"
     end
diff --git a/lib/bundler/source/rubygems.rb b/lib/bundler/source/rubygems.rb
index b37bfbccb9..5dceacbae4 100644
--- a/lib/bundler/source/rubygems.rb
+++ b/lib/bundler/source/rubygems.rb
@@ -499,7 +499,7 @@ module Bundler
       end
 
       def rubygems_dir
-        Bundler.rubygems.gem_dir
+        Bundler.bundle_path
       end
 
       def default_cache_path_for(dir)
diff --git a/lib/bundler/stub_specification.rb b/lib/bundler/stub_specification.rb
index fa071901e5..88a4257fa4 100644
--- a/lib/bundler/stub_specification.rb
+++ b/lib/bundler/stub_specification.rb
@@ -64,9 +64,11 @@ module Bundler
     end
 
     def full_gem_path
-      # deleted gems can have their stubs return nil, so in that case grab the
-      # expired path from the full spec
-      stub.full_gem_path || method_missing(:full_gem_path)
+      stub.full_gem_path
+    end
+
+    def full_gem_path=(path)
+      stub.full_gem_path = path
     end
 
     def full_require_paths
diff --git a/lib/bundler/version.rb b/lib/bundler/version.rb
index 492cd1d751..9e8fa48a1d 100644
--- a/lib/bundler/version.rb
+++ b/lib/bundler/version.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: false
 
 module Bundler
-  VERSION = "2.3.14".freeze
+  VERSION = "2.3.15".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 0b83b1f0ed..8c2c465ad4 100644
--- a/lib/rubygems.rb
+++ b/lib/rubygems.rb
@@ -8,7 +8,7 @@
 require 'rbconfig'
 
 module Gem
-  VERSION = "3.3.14".freeze
+  VERSION = "3.3.15".freeze
 end
 
 # Must be first since it unloads the prelude from 1.9.2
diff --git a/lib/rubygems/command_manager.rb b/lib/rubygems/command_manager.rb
index 03cdd6a4bb..e421f89884 100644
--- a/lib/rubygems/command_manager.rb
+++ b/lib/rubygems/command_manager.rb
@@ -148,7 +148,12 @@ class Gem::CommandManager
   def run(args, build_args=nil)
     process_args(args, build_args)
   rescue StandardError, Timeout::Error => ex
-    alert_error clean_text("While executing gem ... (#{ex.class})\n    #{ex}")
+    if ex.respond_to?(:detailed_message)
+      msg = ex.detailed_message(highlight: false).sub(/\A(.*?)(?: \(.+?\))/) { $1 }
+    else
+      msg = ex.message
+    end
+    alert_error clean_text("While executing gem ... (#{ex.class})\n    #{msg}")
     ui.backtrace ex
 
     terminate_interaction(1)
diff --git a/lib/rubygems/commands/update_command.rb b/lib/rubygems/commands/update_command.rb
index 42d6f6046b..54b1251010 100644
--- a/lib/rubygems/commands/update_command.rb
+++ b/lib/rubygems/commands/update_command.rb
@@ -173,10 +173,11 @@ command to remove old versions.
     highest_remote_gem.first
   end
 
-  def install_rubygems(version) # :nodoc:
+  def install_rubygems(spec) # :nodoc:
     args = update_rubygems_arguments
+    version = spec.version
 
-    update_dir = File.join Gem.dir, 'gems', "rubygems-update-#{version}"
+    update_dir = File.join spec.base_dir, 'gems', "rubygems-update-#{version}"
 
     Dir.chdir update_dir do
       say "Installing RubyGems #{version}" unless options[:silent]
@@ -290,9 +291,7 @@ command to remove old versions.
     installed_gems = update_gem('rubygems-update', version) if installed_gems.empty? || installed_gems.first.version != version
     return if installed_gems.empty?
 
-    version = installed_gems.first.version
-
-    install_rubygems version
+    install_rubygems installed_gems.first
   end
 
   def update_rubygems_arguments # :nodoc:
diff --git a/lib/rubygems/specification.rb b/lib/rubygems/specification.rb
index 9b533caf54..33eb0a2bff 100644
--- a/lib/rubygems/specification.rb
+++ b/lib/rubygems/specification.rb
@@ -1270,7 +1270,14 @@ class Gem::Specification < Gem::BasicSpecification
   def self._load(str)
     Gem.load_yaml
 
-    array = Marshal.load str
+    array = begin
+      Marshal.load str
+    rescue ArgumentError => e
+      raise unless e.message.include?("YAML")
+
+      Object.const_set "YAML", Psych
+      Marshal.load str
+    end
 
     spec = Gem::Specification.new
     spec.instance_variable_set :@specification_version, array[1]
@@ -1289,11 +1296,6 @@ class Gem::Specification < Gem::BasicSpecification
       raise TypeError, "invalid Gem::Specification format #{array.inspect}"
     end
 
-    # Cleanup any Psych::PrivateType. They only show up for an old bug
-    # where nil => null, so just convert them to nil based on the type.
-
-    array.map! {|e| e.kind_of?(Psych::PrivateType) ? nil : e }
-
     spec.instance_variable_set :@rubygems_version,          array[0]
     # spec version
     spec.instance_variable_set :@name,                      array[2]
diff --git a/spec/bundler/commands/clean_spec.rb b/spec/bundler/commands/clean_spec.rb
index 576872b0f6..db81c10e9d 100644
--- a/spec/bundler/commands/clean_spec.rb
+++ b/spec/bundler/commands/clean_spec.rb
@@ -208,7 +208,7 @@ RSpec.describe "bundle clean" do
     G
 
     FileUtils.mkdir_p(bundled_app("real-path"))
-    FileUtils.ln_sf(bundled_app("real-path"), bundled_app("symlink-path"))
+    File.symlink(bundled_app("real-path"), bundled_app("symlink-path"))
 
     bundle "config set path #{bundled_app("symlink-path")}"
     bundle "install"
diff --git a/spec/bundler/commands/config_spec.rb b/spec/bundler/commands/config_spec.rb
index fb7aa3cc67..6148b1c7ce 100644
--- a/spec/bundler/commands/config_spec.rb
+++ b/spec/bundler/commands/config_spec.rb
@@ -435,6 +435,34 @@ E
     end
   end
 
+  describe "commented out settings with urls" do
+    before do
+      bundle "config set #mirror.https://rails-assets.org http://localhost:9292"
+    end
+
+    it "does not make bundler crash and ignores the configuration" do
+      bundle "config list --parseable"
+
+      expect(out).to eq("#mirror.https://rails-assets.org/=http://localhost:9292")
+      expect(err).to be_empty
+
+      ruby(<<~RUBY)
+        require "#{entrypoint}"
+        print Bundler.settings.mirror_for("https://rails-assets.org")
+      RUBY
+      expect(out).to eq("https://rails-assets.org/")
+      expect(err).to be_empty
+
+      bundle "config set mirror.all http://localhost:9293"
+      ruby(<<~RUBY)
+        require "#{entrypoint}"
+        print Bundler.settings.mirror_for("https://rails-assets.org")
+      RUBY
+      expect(out).to eq("http://localhost:9293/")
+      expect(err).to be_empty
+    end
+  end
+
   describe "subcommands" do
     it "list" do
       bundle "config list", :env => { "BUNDLE_FOO" => "bar" }
diff --git a/spec/bundler/commands/install_spec.rb b/spec/bundler/commands/install_spec.rb
index f189a70b10..4a48187db0 100644
--- a/spec/bundler/commands/install_spec.rb
+++ b/spec/bundler/commands/install_spec.rb
@@ -755,12 +755,8 @@ RSpec.describe "bundle install with gem sources" do
       end
 
       expect(err).not_to include("ERROR REPORT TEMPLATE")
-
-      expect(err).to include(
-        "There was an error while trying to delete `#{foo_path}`. " \
-        "It is likely that you need to grant executable permissions for all parent directories " \
-        "and write permissions for `#{gems_path}`, and the same thing for all subdirectories inside #{foo_path}."
-      )
+      expect(err).to include("Could not delete previous installation of `#{foo_path}`.")
+      expect(err).to include("The underlying error was Errno::EACCES")
     end
   end
 
@@ -973,4 +969,37 @@ RSpec.describe "bundle install with gem sources" do
       expect(last_command).to be_success
     end
   end
+
+  context "with a symlinked configured as bundle path and a gem with symlinks" do
+    before do
+      symlinked_bundled_app = tmp("bundled_app-symlink")
+      File.symlink(bundled_app, symlinked_bundled_app)
+      bundle "config path #{File.join(symlinked_bundled_app, ".vendor")}"
+
+      binman_path = tmp("binman")
+      FileUtils.mkdir_p binman_path
+
+      readme_path = File.join(binman_path, "README.markdown")
+      FileUtils.touch(readme_path)
+
+      man_path = File.join(binman_path, "man", "man0")
+      FileUtils.mkdir_p man_path
+
+      File.symlink("../../README.markdown", File.join(man_path, "README.markdown"))
+
+      build_repo4 do
+        build_gem "binman", :path => gem_repo4("gems"), :lib_path => binman_path, :no_default => true do |s|
+          s.files = ["README.markdown", "man/man0/README.markdown"]
+        end
+      end
+    end
+
+    it "installs fine" do
+      install_gemfile <<~G
+        source "#{file_uri_for(gem_repo4)}"
+
+        gem "binman"
+      G
+    end
+  end
 end
diff --git a/spec/bundler/commands/remove_spec.rb b/spec/bundler/commands/remove_spec.rb
index 95d6e75e9f..ceba6c5ede 100644
--- a/spec/bundler/commands/remove_spec.rb
+++ b/spec/bundler/commands/remove_spec.rb
@@ -13,6 +13,36 @@ RSpec.describe "bundle remove" do
     end
   end
 
+  context "after 'bundle install' is run" do
+    describe "running 'bundle remove GEM_NAME'" do
+      it "removes it from the lockfile" do
+        rack_dep = <<~L
+
+          DEPENDENCIES
+            rack
+
+        L
+
+        gemfile <<-G
+          source "#{file_uri_for(gem_repo1)}"
+
+          gem "rack"
+        G
+
+        bundle "install"
+
+        expect(lockfile).to include(rack_dep)
+
+        bundle "remove rack"
+
+        expect(gemfile).to eq <<~G
+          source "#{file_uri_for(gem_repo1)}"
+        G
+        expect(lockfile).to_not include(rack_dep)
+      end
+    end
+  end
+
   context "when --install flag is specified", :bundler => "< 3" do
     it "removes gems from .bundle" do
       gemfile <<-G
diff --git a/spec/bundler/install/gemfile/sources_spec.rb b/spec/bundler/install/gemfile/sources_spec.rb
index 62cad6800f..89c812e5d5 100644
--- a/spec/bundler/install/gemfile/sources_spec.rb
+++ b/spec/bundler/install/gemfile/sources_spec.rb
@@ -1255,6 +1255,32 @@ RSpec.describe "bundle install with gems on multiple sources" do
     end
   end
 
+  context "when Gemfile overrides a gemspec development dependency to change the default source" do
+    before do
+      build_repo4 do
+        build_gem "bar"
+      end
+
+      build_lib("gemspec_test", :path => tmp.join("gemspec_test")) do |s|
+        s.add_development_dependency "bar"
+      end
+
+      install_gemfile <<-G, :artifice => "compact_index"
+        source "https://gem.repo1"
+
+        source "https://gem.repo4" do
+          gem "bar"
+        end
+
+        gemspec :path => "#{tmp.join("gemspec_test")}"
+      G
+    end
+
+    it "does not print warnings" do
+      expect(err).to be_empty
+    end
+  end
+
   it "doesn't update version when a gem uses a source block but a higher version from another source is already installed locally" do
     build_repo2 do
       build_gem "example", "0.1.0"
diff --git a/spec/bundler/install/gems/flex_spec.rb b/spec/bundler/install/gems/flex_spec.rb
index f9b374cf01..28ffaff3d5 100644
--- a/spec/bundler/install/gems/flex_spec.rb
+++ b/spec/bundler/install/gems/flex_spec.rb
@@ -156,7 +156,7 @@ RSpec.describe "bundle flex_install" do
     end
   end
 
-  describe "when Gemfile conflicts with lockfile" do
+  describe "when running bundle install and Gemfile conflicts with lockfile" do
     before(:each) do
       build_repo2
       install_gemfile <<-G
@@ -190,7 +190,7 @@ RSpec.describe "bundle flex_install" do
       expect(err).to match(/could not find gem 'rack-obama/i)
     end
 
-    it "suggests bundle update when the Gemfile requires different versions than the lock" do
+    it "suggests deleting the Gemfile.lock file when the Gemfile requires different versions than the lock" do
       bundle "config set force_ruby_platform true"
 
       nice_error = <<-E.strip.gsub(/^ {8}/, "")
@@ -205,7 +205,7 @@ RSpec.describe "bundle flex_install" do
             rack_middleware was resolved to 1.0, which depends on
               rack (= 0.9.1)
 
-        Running `bundle update` will rebuild your snapshot from scratch, using only
+        Deleting your Gemfile.lock file and running `bundle install` will rebuild your snapshot from scratch, using only
         the gems in your Gemfile, which may resolve the conflict.
       E
 
@@ -214,6 +214,67 @@ RSpec.describe "bundle flex_install" do
     end
   end
 
+  describe "when running bundle update and Gemfile conflicts with lockfile" do
+    before(:each) do
+      build_repo4 do
+        build_gem "jekyll-feed", "0.16.0"
+        build_gem "jekyll-feed", "0.15.1"
+
+        build_gem "github-pages", "226" do |s|
+          s.add_dependency "jekyll-feed", "0.15.1"
+        end
+      end
+
+      install_gemfile <<-G
+        source "#{file_uri_for(gem_repo4)}"
+        gem "jekyll-feed", "~> 0.12"
+      G
+
+      puts lockfile
+      lockfile <<-L
+        GEM
+          remote: #{file_uri_for(gem_repo4)}/
+          specs:
+            jekyll-feed (0.16.0)
+
+        PLATFORMS
+          #{lockfile_platforms}
+
+        DEPENDENCIES
+          jekyll-feed
+
+        BUNDLED WITH
+           #{Bundler::VERSION}
+      L
+
+      gemfile <<-G
+        source "#{file_uri_for(gem_repo4)}"
+        gem "github-pages", "~> 226"
+        gem "jekyll-feed", "~> 0.12"
+      G
+    end
+
+    it "suggests deleting the Gemfile.lock file when the Gemfile requires different versions than the lock" do
+      nice_error = <<-E.strip.gsub(/^ {8}/, "")
+        Bundler could not find compatible versions for gem "jekyll-feed":
+          In snapshot (Gemfile.lock):
+            jekyll-feed (>= 0.16.0)
+
+          In Gemfile:
+            jekyll-feed (~> 0.12)
+
+            github-pages (~> 226) was resolved to 226, which depends on
+              jekyll-feed (= 0.15.1)
+
+        Deleting your Gemfile.lock file and running `bundle install` will rebuild your snapshot from scratch, using only
+        the gems in your Gemfile, which may resolve the conflict.
+      E
+
+      bundle :update, :raise_on_error => false
+      expect(err).to end_with(nice_error)
+    end
+  end
+
   describe "subtler cases" do
     before :each do
       install_gemfile <<-G
diff --git a/spec/bundler/install/gems/resolving_spec.rb b/spec/bundler/install/gems/resolving_spec.rb
index 469ecd412f..f23d137bc1 100644
--- a/spec/bundler/install/gems/resolving_spec.rb
+++ b/spec/bundler/install/gems/resolving_spec.rb
@@ -282,6 +282,27 @@ RSpec.describe "bundle install with install-time dependencies" do
         expect(err).not_to include("That means the author of parallel_tests (3.8.0) has removed it.")
       end
 
+      it "gives a meaningful error on ruby version mismatches between dependencies" do
+        build_repo4 do
+          build_gem "requires-old-ruby" do |s|
+            s.required_ruby_version = "< #{RUBY_VERSION}"
+          end
+        end
+
+        build_lib("foo", :path => bundled_app) do |s|
+          s.required_ruby_version = ">= #{RUBY_VERSION}"
+
+          s.add_dependency "requires-old-ruby"
+        end
+
+        install_gemfile <<-G, :raise_on_error => false
+          source "#{file_uri_for(gem_repo4)}"
+          gemspec
+        G
+
+        expect(err).to include("Bundler found conflicting requirements for the Ruby\0 version:")
+      end
+
       it "installs the older version under rate limiting conditions" do
         build_repo4 do
           build_gem "rack", "9001.0.0" do |s|
diff --git a/spec/bundler/install/gems/standalone_spec.rb b/spec/bundler/install/gems/standalone_spec.rb
index 5cbb484c68..0bbd829148 100644
--- a/spec/bundler/install/gems/standalone_spec.rb
+++ b/spec/bundler/install/gems/standalone_spec.rb
@@ -147,9 +147,16 @@ RSpec.shared_examples "bundle install --standalone" do
       bundle "lock", :dir => cwd, :artifice => "compact_index"
     end
 
-    it "works" do
+    it "works and points to the vendored copies, not to the default copies" do
       bundle "config set --local path #{bundled_app("bundle")}"
       bundle :install, :standalone => true, :dir => cwd, :artifice => "compact_index", :env => { "BUNDLER_GEM_DEFAULT_DIR" => system_gem_path.to_s }
+
+      load_path_lines = bundled_app("bundle/bundler/setup.rb").read.split("\n").select {|line| line.start_with?("$:.unshift") }
+
+      expect(load_path_lines).to eq [
+        '$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{RbConfig::CONFIG["ruby_version"]}/gems/bar-1.0.0/lib")',
+        '$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{RbConfig::CONFIG["ruby_version"]}/gems/foo-1.0.0/lib")',
+      ]
     end
   end
 
diff --git a/spec/bundler/install/process_lock_spec.rb b/spec/bundler/install/process_lock_spec.rb
index dac0d34bc4..1f8c62f26e 100644
--- a/spec/bundler/install/process_lock_spec.rb
+++ b/spec/bundler/install/process_lock_spec.rb
@@ -31,5 +31,27 @@ RSpec.describe "process lock spec" do
         expect(processed).to eq true
       end
     end
+
+    context "when creating a lock raises Errno::EPERM" do
+      before { allow(File).to receive(:open).and_raise(Errno::EPERM) }
+
+      it "skips creating the lock file and yields" do
+        processed = false
+        Bundler::ProcessLock.lock(default_bundle_path) { processed = true }
+
+        expect(processed).to eq true
+      end
+    end
+
+    context "when creating a lock raises Errno::EROFS" do
+      before { allow(File).to receive(:open).and_raise(Errno::EROFS) }
+
+      it "skips creating the lock file and yields" do
+        processed = false
+        Bundler::ProcessLock.lock(default_bundle_path) { processed = true }
+
+        expect(processed).to eq true
+      end
+    end
   end
 end
diff --git a/spec/bundler/runtime/setup_spec.rb b/spec/bundler/runtime/setup_spec.rb
index 35873dcaa9..91f8aaf78a 100644
--- a/spec/bundler/runtime/setup_spec.rb
+++ b/spec/bundler/runtime/setup_spec.rb
@@ -1,7 +1,6 @@
 # frozen_string_literal: true
 
 require "tmpdir"
-require "tempfile"
 
 RSpec.describe "Bundler.setup" do
   describe "with no arguments" do
@@ -800,7 +799,7 @@ end
       run <<~RUBY
         puts ENV['MANPATH']
         require "open3"
-        puts Open3.capture2e("man", "ls")[0]
+        puts Open3.capture2e({ "LC_ALL" => "C" }, "man", "ls")[0]
       RUBY
 
       lines = out.split("\n")
@@ -861,19 +860,17 @@ end
 
   context "with bundler is located in symlinked GEM_HOME" do
     let(:gem_home) { Dir.mktmpdir }
-    let(:symlinked_gem_home) { Tempfile.new("gem_home").path }
+    let(:symlinked_gem_home) { tmp("gem_home-symlink").to_s }
     let(:full_name) { "bundler-#{Bundler::VERSION}" }
 
     before do
-      skip "symlink destination exists" if Gem.win_platform?
-
-      FileUtils.ln_sf(gem_home, symlinked_gem_home)
+      File.symlink(gem_home, symlinked_gem_home)
       gems_dir = File.join(gem_home, "gems")
       specifications_dir = File.join(gem_home, "specifications")
       Dir.mkdir(gems_dir)
       Dir.mkdir(specifications_dir)
 
-      FileUtils.ln_s(source_root, File.join(gems_dir, full_name))
+      File.symlink(source_root, File.join(gems_dir, full_name))
 
       gemspec_content = File.binread(gemspec).
                 sub("Bundler::VERSION", %("#{Bundler::VERSION}")).
diff --git a/spec/bundler/spec_helper.rb b/spec/bundler/spec_helper.rb
index dce2939e83..23db133b67 100644
--- a/spec/bundler/spec_helper.rb
+++ b/spec/bundler/spec_helper.rb
@@ -113,6 +113,10 @@ RSpec.configure do |config|
     end
   end
 
+  config.before :each, :sudo => true do
+    Spec::Sudo.write_safe_config
+  end
+
   config.after :suite do
     FileUtils.rm_r Spec::Path.pristine_system_gem_path
   end
diff --git a/spec/bundler/support/builders.rb b/spec/bundler/support/builders.rb
index aca31638ac..91f0106d7d 100644
--- a/spec/bundler/support/builders.rb
+++ b/spec/bundler/support/builders.rb
@@ -484,7 +484,7 @@ module Spec
         end
 
         @spec.authors = ["no one"]
-        @spec.files = @files.keys
+        @spec.files += @files.keys
 
         case options[:gemspec]
         when false
@@ -589,7 +589,8 @@ module Spec
 
     class GemBuilder < LibBuilder
       def _build(opts)
-        lib_path = super(opts.merge(:path => @context.tmp(".tmp/#{@spec.full_name}"), :no_default => opts[:no_default]))
+        lib_path = opts[:lib_path] || @context.tmp(".tmp/#{@spec.full_name}")
+        lib_path = super(opts.merge(:path => lib_path, :no_default => opts[:no_default]))
         destination = opts[:path] || _default_path
         FileUtils.mkdir_p(lib_path.join(destination))
 
diff --git a/spec/bundler/support/path.rb b/spec/bundler/support/path.rb
index 41b36997b2..a39e46c78a 100644
--- a/spec/bundler/support/path.rb
+++ b/spec/bundler/support/path.rb
@@ -258,6 +258,10 @@ module Spec
       end
     end
 
+    def git_root
+      ruby_core? ? source_root : source_root.parent
+    end
+
     private
 
     def git_ls_files(glob)
@@ -278,10 +282,6 @@ module Spec
       ruby_core? ? "man/bundle* man/gemfile*" : "lib/bundler/man/bundle*.1 lib/bundler/man/gemfile*.5"
     end
 
-    def git_root
-      ruby_core? ? source_root : source_root.parent
-    end
-
     def ruby_core_tarball?
       !git_root.join(".git").directory?
     end
diff --git a/spec/bundler/support/sudo.rb b/spec/bundler/support/sudo.rb
index 04e9443945..7b9b392754 100644
--- a/spec/bundler/support/sudo.rb
+++ b/spec/bundler/support/sudo.rb
@@ -6,6 +6,10 @@ module Spec
       @which_sudo ||= Bundler.which("sudo")
     end
 
+    def self.write_safe_config
+      File.write(Spec::Path.tmp("gitconfig"), "[safe]\n\tdirectory = #{Spec::Path.git_root}")
+    end
+
     def sudo(cmd)
       raise "sudo not present" unless Sudo.present?
       sys_exec("sudo #{cmd}")
diff --git a/test/rubygems/data/null-type.gemspec.rz b/test/rubygems/data/null-type.gemspec.rz
index 2134fcde29..58fc1ed8a0 100644
--- a/test/rubygems/data/null-type.gemspec.rz
+++ b/test/rubygems/data/null-type.gemspec.rz
diff --git a/test/rubygems/test_gem_command_manager.rb b/test/rubygems/test_gem_command_manager.rb
index bee635d67e..00197d10f7 100644
--- a/test/rubygems/test_gem_command_manager.rb
+++ b/test/rubygems/test_gem_command_manager.rb
@@ -80,7 +80,13 @@ class TestGemCommandManager < Gem::TestCase
       message << "\nDid you mean?  \"push\""
     end
 
-    assert_equal message, e.message
+    if e.respond_to?(:detailed_message)
+      actual_message = e.detailed_message(highlight: false).sub(/\A(.*?)(?: \(.+?\))/) { $1 }
+    else
+      actual_message = e.message
+    end
+
+    assert_equal message, actual_message
   end
 
   def test_run_interrupt
diff --git a/test/rubygems/test_gem_commands_update_command.rb b/test/rubygems/test_gem_commands_update_command.rb
index c765e9a8df..b5e9f004d1 100644
--- a/test/rubygems/test_gem_commands_update_command.rb
+++ b/test/rubygems/test_gem_commands_update_command.rb
@@ -191,6 +191,37 @@ class TestGemCommandsUpdateCommand < Gem::TestCase
     assert_empty out
   end
 
+  def test_execute_system_update_installed_in_non_default_gem_path
+    rubygems_update_spec = quick_gem "rubygems-update", 9 do |s|
+      write_file File.join(@tempdir, 'setup.rb')
+
+      s.files += %w[setup.rb]
+    end
+
+    util_setup_spec_fetcher rubygems_update_spec
+
+    rubygems_update_package = Gem::Package.build rubygems_update_spec
+
+    gemhome2 = "#{@gemhome}2"
+
+    Gem::Installer.at(rubygems_update_package, :install_dir => gemhome2).install
+
+    Gem.use_paths @gemhome, [gemhome2, @gemhome]
+
+    @cmd.options[:args]          = []
+    @cmd.options[:system]        = true
+
+    use_ui @ui do
+      @cmd.execute
+    end
+
+    out = @ui.output.split "\n"
+    assert_equal "Installing RubyGems 9", out.shift
+    assert_equal "RubyGems system software updated", out.shift
+
+    assert_empty out
+  end
+
   def test_execute_system_specific
     spec_fetcher do |fetcher|
       fetcher.download 'rubygems-update', 8 do |s|
diff --git a/test/rubygems/test_gem_specification.rb b/test/rubygems/test_gem_specification.rb
index 8b0477c4dd..ccb81caf37 100644
--- a/test/rubygems/test_gem_specification.rb
+++ b/test/rubygems/test_gem_specification.rb
@@ -1072,7 +1072,7 @@ dependencies: []
 
     data = Marshal.load Gem::Util.inflate(Gem.read_binary(path))
 
-    assert_nil data.signing_key
+    assert_instance_of Gem::Specification, data
   end
 
   def test_initialize
diff --git a/tool/bundler/dev_gems.rb.lock b/tool/bundler/dev_gems.rb.lock
index c467b988f6..fc48d3e05f 100644
--- a/tool/bundler/dev_gems.rb.lock
+++ b/tool/bundler/dev_gems.rb.lock
@@ -72,4 +72,4 @@ DEPENDENCIES
   webrick (~> 1.6)
 
 BUNDLED WITH
-   2.3.14
+   2.3.15
diff --git a/tool/bundler/rubocop_gems.rb.lock b/tool/bundler/rubocop_gems.rb.lock
index 0e2e34793f..4027570ebb 100644
--- a/tool/bundler/rubocop_gems.rb.lock
+++ b/tool/bundler/rubocop_gems.rb.lock
@@ -60,4 +60,4 @@ DEPENDENCIES
   test-unit
 
 BUNDLED WITH
-   2.3.14
+   2.3.15
diff --git a/tool/bundler/standard_gems.rb.lock b/tool/bundler/standard_gems.rb.lock
index fa8daf69de..b939fa05d6 100644
--- a/tool/bundler/standard_gems.rb.lock
+++ b/tool/bundler/standard_gems.rb.lock
@@ -66,4 +66,4 @@ DEPENDENCIES
   test-unit
 
 BUNDLED WITH
-   2.3.14
+   2.3.15
diff --git a/tool/bundler/test_gems.rb.lock b/tool/bundler/test_gems.rb.lock
index 05f88ccd98..dab017efc8 100644
--- a/tool/bundler/test_gems.rb.lock
+++ b/tool/bundler/test_gems.rb.lock
@@ -41,4 +41,4 @@ DEPENDENCIES
   webrick (= 1.7.0)
 
 BUNDLED WITH
-   2.3.14
+   2.3.15