diff --git a/lib/bundler.rb b/lib/bundler.rb
index a7d5d1e64a6349..b88bab8f0af26a 100644
--- a/lib/bundler.rb
+++ b/lib/bundler.rb
@@ -236,8 +236,9 @@ def user_home
         end
 
         if warning
-          user_home = tmp_home_path(warning)
-          Bundler.ui.warn "#{warning}\nBundler will use `#{user_home}' as your home directory temporarily.\n"
+          Bundler.ui.warn "#{warning}\n"
+          user_home = tmp_home_path
+          Bundler.ui.warn "Bundler will use `#{user_home}' as your home directory temporarily.\n"
           user_home
         else
           Pathname.new(home)
@@ -684,15 +685,13 @@ def configure_gem_home
       Bundler.rubygems.clear_paths
     end
 
-    def tmp_home_path(warning)
+    def tmp_home_path
       Kernel.send(:require, "tmpdir")
       SharedHelpers.filesystem_access(Dir.tmpdir) do
         path = Bundler.tmp
         at_exit { Bundler.rm_rf(path) }
         path
       end
-    rescue RuntimeError => e
-      raise e.exception("#{warning}\nBundler also failed to create a temporary home directory':\n#{e}")
     end
 
     # @param env [Hash]
diff --git a/lib/bundler/definition.rb b/lib/bundler/definition.rb
index 8998e3b3ae2028..b585b06df10247 100644
--- a/lib/bundler/definition.rb
+++ b/lib/bundler/definition.rb
@@ -138,7 +138,7 @@ def initialize(lockfile, dependencies, sources, unlock, ruby_version = nil, opti
         @unlock[:gems] ||= @dependencies.map(&:name)
       else
         eager_unlock = expand_dependencies(@unlock[:gems] || [], true)
-        @unlock[:gems] = @locked_specs.for(eager_unlock, [], false, false, false).map(&:name)
+        @unlock[:gems] = @locked_specs.for(eager_unlock, false, false, false).map(&:name)
       end
 
       @dependency_changes = converge_dependencies
@@ -190,25 +190,15 @@ def resolve_remotely!
     #
     # @return [Bundler::SpecSet]
     def specs
-      @specs ||= begin
-        begin
-          specs = resolve.materialize(requested_dependencies)
-        rescue GemNotFound => e # Handle yanked gem
-          gem_name, gem_version = extract_gem_info(e)
-          locked_gem = @locked_specs[gem_name].last
-          raise if locked_gem.nil? || locked_gem.version.to_s != gem_version || !@remote
-          raise GemNotFound, "Your bundle is locked to #{locked_gem} from #{locked_gem.source}, but that version can " \
-                             "no longer be found in that source. That means the author of #{locked_gem} has removed it. " \
-                             "You'll need to update your bundle to a version other than #{locked_gem} that hasn't been " \
-                             "removed in order to install."
-        end
-        unless specs["bundler"].any?
-          bundler = sources.metadata_source.specs.search(Gem::Dependency.new("bundler", VERSION)).last
-          specs["bundler"] = bundler
-        end
-
-        specs
-      end
+      @specs ||= add_bundler_to(resolve.materialize(requested_dependencies))
+    rescue GemNotFound => e # Handle yanked gem
+      gem_name, gem_version = extract_gem_info(e)
+      locked_gem = @locked_specs[gem_name].last
+      raise if locked_gem.nil? || locked_gem.version.to_s != gem_version || !@remote
+      raise GemNotFound, "Your bundle is locked to #{locked_gem} from #{locked_gem.source}, but that version can " \
+                         "no longer be found in that source. That means the author of #{locked_gem} has removed it. " \
+                         "You'll need to update your bundle to a version other than #{locked_gem} that hasn't been " \
+                         "removed in order to install."
     end
 
     def new_specs
@@ -240,17 +230,11 @@ def missing_specs?
     end
 
     def requested_specs
-      @requested_specs ||= begin
-        groups = requested_groups
-        groups.map!(&:to_sym)
-        specs_for(groups)
-      end
+      specs_for(requested_groups)
     end
 
     def requested_dependencies
-      groups = requested_groups
-      groups.map!(&:to_sym)
-      dependencies_for(groups)
+      dependencies_for(requested_groups)
     end
 
     def current_dependencies
@@ -260,11 +244,13 @@ def current_dependencies
     end
 
     def specs_for(groups)
+      groups = requested_groups if groups.empty?
       deps = dependencies_for(groups)
-      SpecSet.new(specs.for(expand_dependencies(deps)))
+      add_bundler_to(resolve.materialize(expand_dependencies(deps)))
     end
 
     def dependencies_for(groups)
+      groups.map!(&:to_sym)
       current_dependencies.reject do |d|
         (d.groups & groups).empty?
       end
@@ -514,6 +500,15 @@ def unlocking?
 
     private
 
+    def add_bundler_to(specs)
+      unless specs["bundler"].any?
+        bundler = sources.metadata_source.specs.search(Gem::Dependency.new("bundler", VERSION)).last
+        specs["bundler"] = bundler
+      end
+
+      specs
+    end
+
     def precompute_source_requirements_for_indirect_dependencies?
       sources.non_global_rubygems_sources.all?(&:dependency_api_available?) && !sources.aggregate_global_source?
     end
@@ -742,7 +737,7 @@ def converge_locked_specs
             # if we won't need the source (according to the lockfile),
             # don't error if the path/git source isn't available
             next if @locked_specs.
-                    for(requested_dependencies, [], false, true, false).
+                    for(requested_dependencies, false, true, false).
                     none? {|locked_spec| locked_spec.source == s.source }
 
             raise
@@ -761,8 +756,8 @@ def converge_locked_specs
       end
 
       resolve = SpecSet.new(converged)
-      @locked_specs_incomplete_for_platform = !resolve.for(expand_dependencies(requested_dependencies & deps), @unlock[:gems], true, true)
-      resolve = SpecSet.new(resolve.for(expand_dependencies(deps, true), [], false, false, false).reject{|s| @unlock[:gems].include?(s.name) })
+      @locked_specs_incomplete_for_platform = !resolve.for(expand_dependencies(requested_dependencies & deps), true, true)
+      resolve = SpecSet.new(resolve.for(expand_dependencies(deps, true), false, false, false).reject{|s| @unlock[:gems].include?(s.name) })
       diff    = nil
 
       # Now, we unlock any sources that do not have anymore gems pinned to it
diff --git a/lib/bundler/dsl.rb b/lib/bundler/dsl.rb
index dc72bf0d9399b9..1605210e55b2b7 100644
--- a/lib/bundler/dsl.rb
+++ b/lib/bundler/dsl.rb
@@ -102,28 +102,26 @@ def gem(name, *args)
       # if there's already a dependency with this name we try to prefer one
       if current = @dependencies.find {|d| d.name == dep.name }
         deleted_dep = @dependencies.delete(current) if current.type == :development
+        return if deleted_dep
 
         if current.requirement != dep.requirement
-          unless deleted_dep
-            return if dep.type == :development
+          return if dep.type == :development
 
-            update_prompt = ""
+          update_prompt = ""
 
-            if File.basename(@gemfile) == Injector::INJECTED_GEMS
-              if dep.requirements_list.include?(">= 0") && !current.requirements_list.include?(">= 0")
-                update_prompt = ". Gem already added"
-              else
-                update_prompt = ". If you want to update the gem version, run `bundle update #{current.name}`"
+          if File.basename(@gemfile) == Injector::INJECTED_GEMS
+            if dep.requirements_list.include?(">= 0") && !current.requirements_list.include?(">= 0")
+              update_prompt = ". Gem already added"
+            else
+              update_prompt = ". If you want to update the gem version, run `bundle update #{current.name}`"
 
-                update_prompt += ". You may also need to change the version requirement specified in the Gemfile if it's too restrictive." unless current.requirements_list.include?(">= 0")
-              end
+              update_prompt += ". You may also need to change the version requirement specified in the Gemfile if it's too restrictive." unless current.requirements_list.include?(">= 0")
             end
-
-            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}"
           end
 
+          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}"
         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" \
@@ -132,12 +130,10 @@ def gem(name, *args)
         end
 
         if current.source != dep.source
-          unless deleted_dep
-            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
+          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
 
diff --git a/lib/bundler/index.rb b/lib/bundler/index.rb
index 36520c0a43d2eb..8930fca6d0fdc1 100644
--- a/lib/bundler/index.rb
+++ b/lib/bundler/index.rb
@@ -195,11 +195,7 @@ def search_by_dependency(dependency, base = nil)
           if base # allow all platforms when searching from a lockfile
             dependency.matches_spec?(spec)
           else
-            if Gem::Platform.respond_to? :match_spec?
-              dependency.matches_spec?(spec) && Gem::Platform.match_spec?(spec)
-            else
-              dependency.matches_spec?(spec) && Gem::Platform.match(spec.platform)
-            end
+            dependency.matches_spec?(spec) && Gem::Platform.match_spec?(spec)
           end
         end
 
diff --git a/lib/bundler/installer/standalone.rb b/lib/bundler/installer/standalone.rb
index 2a3f5cfe35855c..f16135cb481d54 100644
--- a/lib/bundler/installer/standalone.rb
+++ b/lib/bundler/installer/standalone.rb
@@ -3,7 +3,7 @@
 module Bundler
   class Standalone
     def initialize(groups, definition)
-      @specs = groups.empty? ? definition.requested_specs : definition.specs_for(groups.map(&:to_sym))
+      @specs = definition.specs_for(groups)
     end
 
     def generate
diff --git a/lib/bundler/plugin/installer.rb b/lib/bundler/plugin/installer.rb
index 4cb7ddf5d69af2..54ce8528cf03f0 100644
--- a/lib/bundler/plugin/installer.rb
+++ b/lib/bundler/plugin/installer.rb
@@ -77,7 +77,7 @@ def install_all_sources(names, version, git_source_options, rubygems_source)
         source_list = SourceList.new
 
         source_list.add_git_source(git_source_options) if git_source_options
-        source_list.add_global_rubygems_remote(rubygems_source) if rubygems_source
+        Array(rubygems_source).each {|remote| source_list.add_global_rubygems_remote(remote) } if rubygems_source
 
         deps = names.map {|name| Dependency.new name, version }
 
diff --git a/lib/bundler/rubygems_ext.rb b/lib/bundler/rubygems_ext.rb
index 9828fc885c9488..26132078268204 100644
--- a/lib/bundler/rubygems_ext.rb
+++ b/lib/bundler/rubygems_ext.rb
@@ -176,20 +176,36 @@ def hash
     end
   end
 
+  require "rubygems/platform"
+
   class Platform
     JAVA  = Gem::Platform.new("java") unless defined?(JAVA)
     MSWIN = Gem::Platform.new("mswin32") unless defined?(MSWIN)
     MSWIN64 = Gem::Platform.new("mswin64") unless defined?(MSWIN64)
     MINGW = Gem::Platform.new("x86-mingw32") unless defined?(MINGW)
     X64_MINGW = Gem::Platform.new("x64-mingw32") unless defined?(X64_MINGW)
+  end
 
-    undef_method :hash if method_defined? :hash
-    def hash
-      @cpu.hash ^ @os.hash ^ @version.hash
-    end
+  Platform.singleton_class.module_eval do
+    unless Platform.singleton_methods.include?(:match_spec?)
+      def match_spec?(spec)
+        match_gem?(spec.platform, spec.name)
+      end
 
-    undef_method :eql? if method_defined? :eql?
-    alias_method :eql?, :==
+      def match_gem?(platform, gem_name)
+        match_platforms?(platform, Gem.platforms)
+      end
+
+      private
+
+      def match_platforms?(platform, platforms)
+        platforms.any? do |local_platform|
+          platform.nil? ||
+            local_platform == platform ||
+            (local_platform != Gem::Platform::RUBY && local_platform =~ platform)
+        end
+      end
+    end
   end
 
   require "rubygems/util"
diff --git a/lib/bundler/runtime.rb b/lib/bundler/runtime.rb
index e259b590bfc748..287fa1cfe94b8b 100644
--- a/lib/bundler/runtime.rb
+++ b/lib/bundler/runtime.rb
@@ -12,12 +12,10 @@ def initialize(root, definition)
     def setup(*groups)
       @definition.ensure_equivalent_gemfile_and_lockfile if Bundler.frozen_bundle?
 
-      groups.map!(&:to_sym)
-
       # Has to happen first
       clean_load_path
 
-      specs = groups.any? ? @definition.specs_for(groups) : requested_specs
+      specs = @definition.specs_for(groups)
 
       SharedHelpers.set_bundle_environment
       Bundler.rubygems.replace_entrypoints(specs)
diff --git a/lib/bundler/settings.rb b/lib/bundler/settings.rb
index 95da31a76568e7..de42cc16affb40 100644
--- a/lib/bundler/settings.rb
+++ b/lib/bundler/settings.rb
@@ -428,12 +428,8 @@ def printable_value(value, key)
     def global_config_file
       if ENV["BUNDLE_CONFIG"] && !ENV["BUNDLE_CONFIG"].empty?
         Pathname.new(ENV["BUNDLE_CONFIG"])
-      else
-        begin
-          Bundler.user_bundle_path("config")
-        rescue PermissionError, GenericSystemCallError
-          nil
-        end
+      elsif Bundler.rubygems.user_home && !Bundler.rubygems.user_home.empty?
+        Pathname.new(Bundler.rubygems.user_home).join(".bundle/config")
       end
     end
 
diff --git a/lib/bundler/spec_set.rb b/lib/bundler/spec_set.rb
index af16984454ee2f..1a8906c47ee41a 100644
--- a/lib/bundler/spec_set.rb
+++ b/lib/bundler/spec_set.rb
@@ -11,15 +11,14 @@ def initialize(specs)
       @specs = specs
     end
 
-    def for(dependencies, skip = [], check = false, match_current_platform = false, raise_on_missing = true)
+    def for(dependencies, check = false, match_current_platform = false, raise_on_missing = true)
       handled = []
       deps = dependencies.dup
       specs = []
-      skip += ["bundler"]
 
       loop do
         break unless dep = deps.shift
-        next if handled.include?(dep) || skip.include?(dep.name)
+        next if handled.any?{|d| d.name == dep.name && (match_current_platform || d.__platform == dep.__platform) } || dep.name == "bundler"
 
         handled << dep
 
@@ -73,7 +72,7 @@ def to_hash
     end
 
     def materialize(deps, missing_specs = nil)
-      materialized = self.for(deps, [], false, true, !missing_specs)
+      materialized = self.for(deps, false, true, !missing_specs)
 
       materialized.group_by(&:source).each do |source, specs|
         next unless specs.any?{|s| s.is_a?(LazySpecification) }
@@ -195,7 +194,7 @@ def tsort_each_node
     def spec_for_dependency(dep, match_current_platform)
       specs_for_platforms = lookup[dep.name]
       if match_current_platform
-        GemHelpers.select_best_platform_match(specs_for_platforms, Bundler.local_platform)
+        GemHelpers.select_best_platform_match(specs_for_platforms.select{|s| Gem::Platform.match_spec?(s) }, Bundler.local_platform)
       else
         GemHelpers.select_best_platform_match(specs_for_platforms, dep.__platform)
       end
diff --git a/lib/bundler/vendor/connection_pool/lib/connection_pool.rb b/lib/bundler/vendor/connection_pool/lib/connection_pool.rb
index fbcd26c7655566..984c1c3dcb08cf 100644
--- a/lib/bundler/vendor/connection_pool/lib/connection_pool.rb
+++ b/lib/bundler/vendor/connection_pool/lib/connection_pool.rb
@@ -1,14 +1,18 @@
-require_relative 'connection_pool/version'
-require_relative 'connection_pool/timed_stack'
+require "timeout"
+require_relative "connection_pool/version"
 
+class Bundler::ConnectionPool
+  class Error < ::RuntimeError; end
+  class PoolShuttingDownError < ::Bundler::ConnectionPool::Error; end
+  class TimeoutError < ::Timeout::Error; end
+end
 
-# Generic connection pool class for e.g. sharing a limited number of network connections
-# among many threads.  Note: Connections are lazily created.
+# Generic connection pool class for sharing a limited number of objects or network connections
+# among many threads.  Note: pool elements are lazily created.
 #
 # Example usage with block (faster):
 #
 #    @pool = Bundler::ConnectionPool.new { Redis.new }
-#
 #    @pool.with do |redis|
 #      redis.lpop('my-list') if redis.llen('my-list') > 0
 #    end
@@ -34,29 +38,23 @@
 class Bundler::ConnectionPool
   DEFAULTS = {size: 5, timeout: 5}
 
-  class Error < RuntimeError
-  end
-
   def self.wrap(options, &block)
     Wrapper.new(options, &block)
   end
 
   def initialize(options = {}, &block)
-    raise ArgumentError, 'Connection pool requires a block' unless block
+    raise ArgumentError, "Connection pool requires a block" unless block
 
     options = DEFAULTS.merge(options)
 
-    @size = options.fetch(:size)
+    @size = Integer(options.fetch(:size))
     @timeout = options.fetch(:timeout)
 
     @available = TimedStack.new(@size, &block)
-    @key = :"current-#{@available.object_id}"
-    @key_count = :"current-#{@available.object_id}-count"
+    @key = :"pool-#{@available.object_id}"
+    @key_count = :"pool-#{@available.object_id}-count"
   end
 
-if Thread.respond_to?(:handle_interrupt)
-
-  # MRI
   def with(options = {})
     Thread.handle_interrupt(Exception => :never) do
       conn = checkout(options)
@@ -69,28 +67,15 @@ def with(options = {})
       end
     end
   end
-
-else
-
-  # jruby 1.7.x
-  def with(options = {})
-    conn = checkout(options)
-    begin
-      yield conn
-    ensure
-      checkin
-    end
-  end
-
-end
+  alias then with
 
   def checkout(options = {})
     if ::Thread.current[@key]
-      ::Thread.current[@key_count]+= 1
+      ::Thread.current[@key_count] += 1
       ::Thread.current[@key]
     else
-      ::Thread.current[@key_count]= 1
-      ::Thread.current[@key]= @available.pop(options[:timeout] || @timeout)
+      ::Thread.current[@key_count] = 1
+      ::Thread.current[@key] = @available.pop(options[:timeout] || @timeout)
     end
   end
 
@@ -98,64 +83,44 @@ def checkin
     if ::Thread.current[@key]
       if ::Thread.current[@key_count] == 1
         @available.push(::Thread.current[@key])
-        ::Thread.current[@key]= nil
+        ::Thread.current[@key] = nil
+        ::Thread.current[@key_count] = nil
       else
-        ::Thread.current[@key_count]-= 1
+        ::Thread.current[@key_count] -= 1
       end
     else
-      raise Bundler::ConnectionPool::Error, 'no connections are checked out'
+      raise Bundler::ConnectionPool::Error, "no connections are checked out"
     end
 
     nil
   end
 
+  ##
+  # Shuts down the Bundler::ConnectionPool by passing each connection to +block+ and
+  # then removing it from the pool. Attempting to checkout a connection after
+  # shutdown will raise +Bundler::ConnectionPool::PoolShuttingDownError+.
+
   def shutdown(&block)
     @available.shutdown(&block)
   end
 
-  # Size of this connection pool
-  def size
-    @size
+  ##
+  # Reloads the Bundler::ConnectionPool by passing each connection to +block+ and then
+  # removing it the pool. Subsequent checkouts will create new connections as
+  # needed.
+
+  def reload(&block)
+    @available.shutdown(reload: true, &block)
   end
 
+  # Size of this connection pool
+  attr_reader :size
+
   # Number of pool entries available for checkout at this instant.
   def available
     @available.length
   end
-
-  private
-
-  class Wrapper < ::BasicObject
-    METHODS = [:with, :pool_shutdown]
-
-    def initialize(options = {}, &block)
-      @pool = options.fetch(:pool) { ::Bundler::ConnectionPool.new(options, &block) }
-    end
-
-    def with(&block)
-      @pool.with(&block)
-    end
-
-    def pool_shutdown(&block)
-      @pool.shutdown(&block)
-    end
-
-    def pool_size
-      @pool.size
-    end
-
-    def pool_available
-      @pool.available
-    end
-
-    def respond_to?(id, *args)
-      METHODS.include?(id) || with { |c| c.respond_to?(id, *args) }
-    end
-
-    def method_missing(name, *args, &block)
-      with do |connection|
-        connection.send(name, *args, &block)
-      end
-    end
-  end
 end
+
+require_relative "connection_pool/timed_stack"
+require_relative "connection_pool/wrapper"
diff --git a/lib/bundler/vendor/connection_pool/lib/connection_pool/monotonic_time.rb b/lib/bundler/vendor/connection_pool/lib/connection_pool/monotonic_time.rb
deleted file mode 100644
index 8210ab4c415993..00000000000000
--- a/lib/bundler/vendor/connection_pool/lib/connection_pool/monotonic_time.rb
+++ /dev/null
@@ -1,66 +0,0 @@
-# Global monotonic clock from Concurrent Ruby 1.0.
-# Copyright (c) Jerry D'Antonio -- released under the MIT license.
-# Slightly modified; used with permission.
-# https://github.com/ruby-concurrency/concurrent-ruby
-
-require 'thread'
-
-class Bundler::ConnectionPool
-
-  class_definition = Class.new do
-
-    if defined?(Process::CLOCK_MONOTONIC)
-
-      # @!visibility private
-      def get_time
-        Process.clock_gettime(Process::CLOCK_MONOTONIC)
-      end
-
-    elsif defined?(RUBY_ENGINE) && RUBY_ENGINE == 'jruby'
-
-      # @!visibility private
-      def get_time
-        java.lang.System.nanoTime() / 1_000_000_000.0
-      end
-
-    else
-
-      # @!visibility private
-      def initialize
-        @mutex = Thread::Mutex.new
-        @last_time = Time.now.to_f
-      end
-
-      # @!visibility private
-      def get_time
-        @mutex.synchronize do
-          now = Time.now.to_f
-          if @last_time < now
-            @last_time = now
-          else # clock has moved back in time
-            @last_time += 0.000_001
-          end
-        end
-      end
-    end
-  end
-
-  ##
-  # Clock that cannot be set and represents monotonic time since
-  # some unspecified starting point.
-  #
-  # @!visibility private
-  GLOBAL_MONOTONIC_CLOCK = class_definition.new
-  private_constant :GLOBAL_MONOTONIC_CLOCK
-
-  class << self
-    ##
-    # Returns the current time a tracked by the application monotonic clock.
-    #
-    # @return [Float] The current monotonic time when `since` not given else
-    #   the elapsed monotonic time between `since` and the current time
-    def monotonic_time
-      GLOBAL_MONOTONIC_CLOCK.get_time
-    end
-  end
-end
diff --git a/lib/bundler/vendor/connection_pool/lib/connection_pool/timed_stack.rb b/lib/bundler/vendor/connection_pool/lib/connection_pool/timed_stack.rb
index cff8477c1fd36d..a7b1cf06a8f8df 100644
--- a/lib/bundler/vendor/connection_pool/lib/connection_pool/timed_stack.rb
+++ b/lib/bundler/vendor/connection_pool/lib/connection_pool/timed_stack.rb
@@ -1,13 +1,3 @@
-require 'thread'
-require 'timeout'
-require_relative 'monotonic_time'
-
-##
-# Raised when you attempt to retrieve a connection from a pool that has been
-# shut down.
-
-class Bundler::ConnectionPool::PoolShuttingDownError < RuntimeError; end
-
 ##
 # The TimedStack manages a pool of homogeneous connections (or any resource
 # you wish to manage).  Connections are created lazily up to a given maximum
@@ -25,7 +15,7 @@ class Bundler::ConnectionPool::PoolShuttingDownError < RuntimeError; end
 #
 #    conn = ts.pop
 #    ts.pop timeout: 5
-#    #=> raises Timeout::Error after 5 seconds
+#    #=> raises Bundler::ConnectionPool::TimeoutError after 5 seconds
 
 class Bundler::ConnectionPool::TimedStack
   attr_reader :max
@@ -59,12 +49,12 @@ def push(obj, options = {})
       @resource.broadcast
     end
   end
-  alias_method :<<, :push
+  alias << push
 
   ##
   # Retrieves a connection from the stack.  If a connection is available it is
   # immediately returned.  If no connection is available within the given
-  # timeout a Timeout::Error is raised.
+  # timeout a Bundler::ConnectionPool::TimeoutError is raised.
   #
   # +:timeout+ is the only checked entry in +options+ and is preferred over
   # the +timeout+ argument (which will be removed in a future release).  Other
@@ -74,7 +64,7 @@ def pop(timeout = 0.5, options = {})
     options, timeout = timeout, 0.5 if Hash === timeout
     timeout = options.fetch :timeout, timeout
 
-    deadline = Bundler::ConnectionPool.monotonic_time + timeout
+    deadline = current_time + timeout
     @mutex.synchronize do
       loop do
         raise Bundler::ConnectionPool::PoolShuttingDownError if @shutdown_block
@@ -83,18 +73,20 @@ def pop(timeout = 0.5, options = {})
         connection = try_create(options)
         return connection if connection
 
-        to_wait = deadline - Bundler::ConnectionPool.monotonic_time
-        raise Timeout::Error, "Waited #{timeout} sec" if to_wait <= 0
+        to_wait = deadline - current_time
+        raise Bundler::ConnectionPool::TimeoutError, "Waited #{timeout} sec" if to_wait <= 0
         @resource.wait(@mutex, to_wait)
       end
     end
   end
 
   ##
-  # Shuts down the TimedStack which prevents connections from being checked
-  # out.  The +block+ is called once for each connection on the stack.
+  # Shuts down the TimedStack by passing each connection to +block+ and then
+  # removing it from the pool. Attempting to checkout a connection after
+  # shutdown will raise +Bundler::ConnectionPool::PoolShuttingDownError+ unless
+  # +:reload+ is +true+.
 
-  def shutdown(&block)
+  def shutdown(reload: false, &block)
     raise ArgumentError, "shutdown must receive a block" unless block_given?
 
     @mutex.synchronize do
@@ -102,6 +94,7 @@ def shutdown(&block)
       @resource.broadcast
 
       shutdown_connections
+      @shutdown_block = nil if reload
     end
   end
 
@@ -121,6 +114,10 @@ def length
 
   private
 
+  def current_time
+    Process.clock_gettime(Process::CLOCK_MONOTONIC)
+  end
+
   ##
   # This is an extension point for TimedStack and is called with a mutex.
   #
@@ -149,6 +146,7 @@ def shutdown_connections(options = nil)
       conn = fetch_connection(options)
       @shutdown_block.call(conn)
     end
+    @created = 0
   end
 
   ##
diff --git a/lib/bundler/vendor/connection_pool/lib/connection_pool/version.rb b/lib/bundler/vendor/connection_pool/lib/connection_pool/version.rb
index b149c0e242e87d..56ebf69902f9c0 100644
--- a/lib/bundler/vendor/connection_pool/lib/connection_pool/version.rb
+++ b/lib/bundler/vendor/connection_pool/lib/connection_pool/version.rb
@@ -1,3 +1,3 @@
 class Bundler::ConnectionPool
-  VERSION = "2.2.2"
+  VERSION = "2.3.0"
 end
diff --git a/lib/bundler/vendor/connection_pool/lib/connection_pool/wrapper.rb b/lib/bundler/vendor/connection_pool/lib/connection_pool/wrapper.rb
new file mode 100644
index 00000000000000..880170c06b04cd
--- /dev/null
+++ b/lib/bundler/vendor/connection_pool/lib/connection_pool/wrapper.rb
@@ -0,0 +1,57 @@
+class Bundler::ConnectionPool
+  class Wrapper < ::BasicObject
+    METHODS = [:with, :pool_shutdown, :wrapped_pool]
+
+    def initialize(options = {}, &block)
+      @pool = options.fetch(:pool) { ::Bundler::ConnectionPool.new(options, &block) }
+    end
+
+    def wrapped_pool
+      @pool
+    end
+
+    def with(&block)
+      @pool.with(&block)
+    end
+
+    def pool_shutdown(&block)
+      @pool.shutdown(&block)
+    end
+
+    def pool_size
+      @pool.size
+    end
+
+    def pool_available
+      @pool.available
+    end
+
+    def respond_to?(id, *args)
+      METHODS.include?(id) || with { |c| c.respond_to?(id, *args) }
+    end
+
+    # rubocop:disable Style/MethodMissingSuper
+    # rubocop:disable Style/MissingRespondToMissing
+    if ::RUBY_VERSION >= "3.0.0"
+      def method_missing(name, *args, **kwargs, &block)
+        with do |connection|
+          connection.send(name, *args, **kwargs, &block)
+        end
+      end
+    elsif ::RUBY_VERSION >= "2.7.0"
+      ruby2_keywords def method_missing(name, *args, &block)
+        with do |connection|
+          connection.send(name, *args, &block)
+        end
+      end
+    else
+      def method_missing(name, *args, &block)
+        with do |connection|
+          connection.send(name, *args, &block)
+        end
+      end
+    end
+    # rubocop:enable Style/MethodMissingSuper
+    # rubocop:enable Style/MissingRespondToMissing
+  end
+end
diff --git a/lib/bundler/vendor/uri/lib/uri.rb b/lib/bundler/vendor/uri/lib/uri.rb
index 00c01bd07bf949..0e574dd2b191f7 100644
--- a/lib/bundler/vendor/uri/lib/uri.rb
+++ b/lib/bundler/vendor/uri/lib/uri.rb
@@ -86,7 +86,6 @@
 # License::
 #  Copyright (c) 2001 akira yamada <akira@ruby-lang.org>
 #  You can redistribute it and/or modify it under the same term as Ruby.
-# Revision:: $Id$
 #
 
 module Bundler::URI
diff --git a/lib/bundler/vendor/uri/lib/uri/common.rb b/lib/bundler/vendor/uri/lib/uri/common.rb
index cc1ab86c2f4eb1..6539e1810f990b 100644
--- a/lib/bundler/vendor/uri/lib/uri/common.rb
+++ b/lib/bundler/vendor/uri/lib/uri/common.rb
@@ -3,7 +3,6 @@
 # = uri/common.rb
 #
 # Author:: Akira Yamada <akira@ruby-lang.org>
-# Revision:: $Id$
 # License::
 #   You can redistribute it and/or modify it under the same term as Ruby.
 #
@@ -61,82 +60,6 @@ def make_components_hash(klass, array_hash)
     module_function :make_components_hash
   end
 
-  # Module for escaping unsafe characters with codes.
-  module Escape
-    #
-    # == Synopsis
-    #
-    #   Bundler::URI.escape(str [, unsafe])
-    #
-    # == Args
-    #
-    # +str+::
-    #   String to replaces in.
-    # +unsafe+::
-    #   Regexp that matches all symbols that must be replaced with codes.
-    #   By default uses <tt>UNSAFE</tt>.
-    #   When this argument is a String, it represents a character set.
-    #
-    # == Description
-    #
-    # Escapes the string, replacing all unsafe characters with codes.
-    #
-    # This method is obsolete and should not be used. Instead, use
-    # CGI.escape, Bundler::URI.encode_www_form or Bundler::URI.encode_www_form_component
-    # depending on your specific use case.
-    #
-    # == Usage
-    #
-    #   require 'bundler/vendor/uri/lib/uri'
-    #
-    #   enc_uri = Bundler::URI.escape("http://example.com/?a=\11\15")
-    #   # => "http://example.com/?a=%09%0D"
-    #
-    #   Bundler::URI.unescape(enc_uri)
-    #   # => "http://example.com/?a=\t\r"
-    #
-    #   Bundler::URI.escape("@?@!", "!?")
-    #   # => "@%3F@%21"
-    #
-    def escape(*arg)
-      warn "Bundler::URI.escape is obsolete", uplevel: 1
-      DEFAULT_PARSER.escape(*arg)
-    end
-    alias encode escape
-    #
-    # == Synopsis
-    #
-    #   Bundler::URI.unescape(str)
-    #
-    # == Args
-    #
-    # +str+::
-    #   String to unescape.
-    #
-    # == Description
-    #
-    # This method is obsolete and should not be used. Instead, use
-    # CGI.unescape, Bundler::URI.decode_www_form or Bundler::URI.decode_www_form_component
-    # depending on your specific use case.
-    #
-    # == Usage
-    #
-    #   require 'bundler/vendor/uri/lib/uri'
-    #
-    #   enc_uri = Bundler::URI.escape("http://example.com/?a=\11\15")
-    #   # => "http://example.com/?a=%09%0D"
-    #
-    #   Bundler::URI.unescape(enc_uri)
-    #   # => "http://example.com/?a=\t\r"
-    #
-    def unescape(*arg)
-      warn "Bundler::URI.unescape is obsolete", uplevel: 1
-      DEFAULT_PARSER.unescape(*arg)
-    end
-    alias decode unescape
-  end # module Escape
-
-  extend Escape
   include REGEXP
 
   @@schemes = {}
@@ -145,6 +68,20 @@ def self.scheme_list
     @@schemes
   end
 
+  #
+  # Construct a Bundler::URI instance, using the scheme to detect the appropriate class
+  # from +Bundler::URI.scheme_list+.
+  #
+  def self.for(scheme, *arguments, default: Generic)
+    if scheme
+      uri_class = @@schemes[scheme.upcase] || default
+    else
+      uri_class = default
+    end
+
+    return uri_class.new(scheme, *arguments)
+  end
+
   #
   # Base class for all Bundler::URI exceptions.
   #
@@ -315,7 +252,7 @@ def self.extract(str, schemes = nil, &block)
   #
   # Returns a Regexp object which matches to Bundler::URI-like strings.
   # The Regexp object returned by this method includes arbitrary
-  # number of capture group (parentheses).  Never rely on it's number.
+  # number of capture group (parentheses).  Never rely on its number.
   #
   # == Usage
   #
@@ -362,7 +299,7 @@ def self.regexp(schemes = nil)
   # If +enc+ is given, convert +str+ to the encoding before percent encoding.
   #
   # This is an implementation of
-  # http://www.w3.org/TR/2013/CR-html5-20130806/forms.html#url-encoded-form-data.
+  # https://www.w3.org/TR/2013/CR-html5-20130806/forms.html#url-encoded-form-data.
   #
   # See Bundler::URI.decode_www_form_component, Bundler::URI.encode_www_form.
   def self.encode_www_form_component(str, enc=nil)
@@ -403,7 +340,7 @@ def self.decode_www_form_component(str, enc=Encoding::UTF_8)
   # This method doesn't handle files.  When you send a file, use
   # multipart/form-data.
   #
-  # This refers http://url.spec.whatwg.org/#concept-urlencoded-serializer
+  # This refers https://url.spec.whatwg.org/#concept-urlencoded-serializer
   #
   #    Bundler::URI.encode_www_form([["q", "ruby"], ["lang", "en"]])
   #    #=> "q=ruby&lang=en"
diff --git a/lib/bundler/vendor/uri/lib/uri/ftp.rb b/lib/bundler/vendor/uri/lib/uri/ftp.rb
index ad39f57d7b6ee4..2252e405d58f12 100644
--- a/lib/bundler/vendor/uri/lib/uri/ftp.rb
+++ b/lib/bundler/vendor/uri/lib/uri/ftp.rb
@@ -3,7 +3,6 @@
 #
 # Author:: Akira Yamada <akira@ruby-lang.org>
 # License:: You can redistribute it and/or modify it under the same term as Ruby.
-# Revision:: $Id$
 #
 # See Bundler::URI for general documentation
 #
diff --git a/lib/bundler/vendor/uri/lib/uri/generic.rb b/lib/bundler/vendor/uri/lib/uri/generic.rb
index 56b09e1d7f79ff..f29ba6cf18b757 100644
--- a/lib/bundler/vendor/uri/lib/uri/generic.rb
+++ b/lib/bundler/vendor/uri/lib/uri/generic.rb
@@ -4,7 +4,6 @@
 #
 # Author:: Akira Yamada <akira@ruby-lang.org>
 # License:: You can redistribute it and/or modify it under the same term as Ruby.
-# Revision:: $Id$
 #
 # See Bundler::URI for general documentation
 #
@@ -1098,7 +1097,7 @@ def merge!(oth)
     #   # => "http://my.example.com/main.rbx?page=1"
     #
     def merge(oth)
-      rel = parser.send(:convert_to_uri, oth)
+      rel = parser.__send__(:convert_to_uri, oth)
 
       if rel.absolute?
         #raise BadURIError, "both Bundler::URI are absolute" if absolute?
@@ -1183,7 +1182,7 @@ def route_from_path(src, dst)
 
     # :stopdoc:
     def route_from0(oth)
-      oth = parser.send(:convert_to_uri, oth)
+      oth = parser.__send__(:convert_to_uri, oth)
       if self.relative?
         raise BadURIError,
           "relative Bundler::URI: #{self}"
@@ -1291,7 +1290,7 @@ def route_from(oth)
     #   #=> #<Bundler::URI::Generic /main.rbx?page=1>
     #
     def route_to(oth)
-      parser.send(:convert_to_uri, oth).route_from(self)
+      parser.__send__(:convert_to_uri, oth).route_from(self)
     end
 
     #
@@ -1405,7 +1404,7 @@ def eql?(oth)
     # Returns an Array of the components defined from the COMPONENT Array.
     def component_ary
       component.collect do |x|
-        self.send(x)
+        self.__send__(x)
       end
     end
     protected :component_ary
@@ -1430,7 +1429,7 @@ def component_ary
     def select(*components)
       components.collect do |c|
         if component.include?(c)
-          self.send(c)
+          self.__send__(c)
         else
           raise ArgumentError,
             "expected of components of #{self.class} (#{self.class.component.join(', ')})"
diff --git a/lib/bundler/vendor/uri/lib/uri/http.rb b/lib/bundler/vendor/uri/lib/uri/http.rb
index b6ca1c51de3226..50d7e427a52b70 100644
--- a/lib/bundler/vendor/uri/lib/uri/http.rb
+++ b/lib/bundler/vendor/uri/lib/uri/http.rb
@@ -3,7 +3,6 @@
 #
 # Author:: Akira Yamada <akira@ruby-lang.org>
 # License:: You can redistribute it and/or modify it under the same term as Ruby.
-# Revision:: $Id$
 #
 # See Bundler::URI for general documentation
 #
diff --git a/lib/bundler/vendor/uri/lib/uri/https.rb b/lib/bundler/vendor/uri/lib/uri/https.rb
index 78dc6bf532d2fb..4fd4e9af7bbabc 100644
--- a/lib/bundler/vendor/uri/lib/uri/https.rb
+++ b/lib/bundler/vendor/uri/lib/uri/https.rb
@@ -3,7 +3,6 @@
 #
 # Author:: Akira Yamada <akira@ruby-lang.org>
 # License:: You can redistribute it and/or modify it under the same term as Ruby.
-# Revision:: $Id$
 #
 # See Bundler::URI for general documentation
 #
diff --git a/lib/bundler/vendor/uri/lib/uri/ldap.rb b/lib/bundler/vendor/uri/lib/uri/ldap.rb
index b707bedb971ad6..6e9e1918f63464 100644
--- a/lib/bundler/vendor/uri/lib/uri/ldap.rb
+++ b/lib/bundler/vendor/uri/lib/uri/ldap.rb
@@ -7,7 +7,6 @@
 # License::
 #   Bundler::URI::LDAP is copyrighted free software by Takaaki Tateishi and Akira Yamada.
 #   You can redistribute it and/or modify it under the same term as Ruby.
-# Revision:: $Id$
 #
 # See Bundler::URI for general documentation
 #
@@ -119,6 +118,7 @@ def initialize(*arg)
 
     # Private method to cleanup +dn+ from using the +path+ component attribute.
     def parse_dn
+      raise InvalidURIError, 'bad LDAP URL' unless @path
       @dn = @path[1..-1]
     end
     private :parse_dn
diff --git a/lib/bundler/vendor/uri/lib/uri/mailto.rb b/lib/bundler/vendor/uri/lib/uri/mailto.rb
index 5b2a4765c812d4..ff7ab7e114cd90 100644
--- a/lib/bundler/vendor/uri/lib/uri/mailto.rb
+++ b/lib/bundler/vendor/uri/lib/uri/mailto.rb
@@ -3,7 +3,6 @@
 #
 # Author:: Akira Yamada <akira@ruby-lang.org>
 # License:: You can redistribute it and/or modify it under the same term as Ruby.
-# Revision:: $Id$
 #
 # See Bundler::URI for general documentation
 #
diff --git a/lib/bundler/vendor/uri/lib/uri/rfc2396_parser.rb b/lib/bundler/vendor/uri/lib/uri/rfc2396_parser.rb
index a0d62ede640e14..e48e164f4c13e7 100644
--- a/lib/bundler/vendor/uri/lib/uri/rfc2396_parser.rb
+++ b/lib/bundler/vendor/uri/lib/uri/rfc2396_parser.rb
@@ -3,7 +3,6 @@
 # = uri/common.rb
 #
 # Author:: Akira Yamada <akira@ruby-lang.org>
-# Revision:: $Id$
 # License::
 #   You can redistribute it and/or modify it under the same term as Ruby.
 #
@@ -208,21 +207,9 @@ def split(uri)
     #   #=> #<Bundler::URI::LDAP ldap://ldap.example.com/dc=example?user=john>
     #
     def parse(uri)
-      scheme, userinfo, host, port,
-        registry, path, opaque, query, fragment = self.split(uri)
-
-      if scheme && Bundler::URI.scheme_list.include?(scheme.upcase)
-        Bundler::URI.scheme_list[scheme.upcase].new(scheme, userinfo, host, port,
-                                           registry, path, opaque, query,
-                                           fragment, self)
-      else
-        Generic.new(scheme, userinfo, host, port,
-                    registry, path, opaque, query,
-                    fragment, self)
-      end
+      Bundler::URI.for(*self.split(uri), self)
     end
 
-
     #
     # == Args
     #
diff --git a/lib/bundler/vendor/uri/lib/uri/rfc3986_parser.rb b/lib/bundler/vendor/uri/lib/uri/rfc3986_parser.rb
index 07ef4391c02b46..2029cfd05677db 100644
--- a/lib/bundler/vendor/uri/lib/uri/rfc3986_parser.rb
+++ b/lib/bundler/vendor/uri/lib/uri/rfc3986_parser.rb
@@ -69,18 +69,7 @@ def split(uri) #:nodoc:
     end
 
     def parse(uri) # :nodoc:
-      scheme, userinfo, host, port,
-        registry, path, opaque, query, fragment = self.split(uri)
-      scheme_list = Bundler::URI.scheme_list
-      if scheme && scheme_list.include?(uc = scheme.upcase)
-        scheme_list[uc].new(scheme, userinfo, host, port,
-                            registry, path, opaque, query,
-                            fragment, self)
-      else
-        Generic.new(scheme, userinfo, host, port,
-                    registry, path, opaque, query,
-                    fragment, self)
-      end
+      Bundler::URI.for(*self.split(uri), self)
     end
 
 
diff --git a/lib/bundler/vendor/uri/lib/uri/version.rb b/lib/bundler/vendor/uri/lib/uri/version.rb
index 56177ef1949d50..f2bb0ebad26db2 100644
--- a/lib/bundler/vendor/uri/lib/uri/version.rb
+++ b/lib/bundler/vendor/uri/lib/uri/version.rb
@@ -1,6 +1,6 @@
 module Bundler::URI
   # :stopdoc:
-  VERSION_CODE = '001000'.freeze
+  VERSION_CODE = '001001'.freeze
   VERSION = VERSION_CODE.scan(/../).collect{|n| n.to_i}.join('.').freeze
   # :startdoc:
 end
diff --git a/lib/bundler/vendor/uri/lib/uri/ws.rb b/lib/bundler/vendor/uri/lib/uri/ws.rb
new file mode 100644
index 00000000000000..58e08bf98e7f6e
--- /dev/null
+++ b/lib/bundler/vendor/uri/lib/uri/ws.rb
@@ -0,0 +1,84 @@
+# frozen_string_literal: false
+# = uri/ws.rb
+#
+# Author:: Matt Muller <mamuller@amazon.com>
+# License:: You can redistribute it and/or modify it under the same term as Ruby.
+#
+# See Bundler::URI for general documentation
+#
+
+require_relative 'generic'
+
+module Bundler::URI
+
+  #
+  # The syntax of WS URIs is defined in RFC6455 section 3.
+  #
+  # Note that the Ruby Bundler::URI library allows WS URLs containing usernames and
+  # passwords. This is not legal as per the RFC, but used to be
+  # supported in Internet Explorer 5 and 6, before the MS04-004 security
+  # update. See <URL:http://support.microsoft.com/kb/834489>.
+  #
+  class WS < Generic
+    # A Default port of 80 for Bundler::URI::WS.
+    DEFAULT_PORT = 80
+
+    # An Array of the available components for Bundler::URI::WS.
+    COMPONENT = %i[
+      scheme
+      userinfo host port
+      path
+      query
+    ].freeze
+
+    #
+    # == Description
+    #
+    # Creates a new Bundler::URI::WS object from components, with syntax checking.
+    #
+    # The components accepted are userinfo, host, port, path, and query.
+    #
+    # The components should be provided either as an Array, or as a Hash
+    # with keys formed by preceding the component names with a colon.
+    #
+    # If an Array is used, the components must be passed in the
+    # order <code>[userinfo, host, port, path, query]</code>.
+    #
+    # Example:
+    #
+    #     uri = Bundler::URI::WS.build(host: 'www.example.com', path: '/foo/bar')
+    #
+    #     uri = Bundler::URI::WS.build([nil, "www.example.com", nil, "/path", "query"])
+    #
+    # Currently, if passed userinfo components this method generates
+    # invalid WS URIs as per RFC 1738.
+    #
+    def self.build(args)
+      tmp = Util.make_components_hash(self, args)
+      super(tmp)
+    end
+
+    #
+    # == Description
+    #
+    # Returns the full path for a WS Bundler::URI, as required by Net::HTTP::Get.
+    #
+    # If the Bundler::URI contains a query, the full path is Bundler::URI#path + '?' + Bundler::URI#query.
+    # Otherwise, the path is simply Bundler::URI#path.
+    #
+    # Example:
+    #
+    #     uri = Bundler::URI::WS.build(path: '/foo/bar', query: 'test=true')
+    #     uri.request_uri #  => "/foo/bar?test=true"
+    #
+    def request_uri
+      return unless @path
+
+      url = @query ? "#@path?#@query" : @path.dup
+      url.start_with?(?/.freeze) ? url : ?/ + url
+    end
+  end
+
+  @@schemes['WS'] = WS
+
+end
diff --git a/lib/bundler/vendor/uri/lib/uri/wss.rb b/lib/bundler/vendor/uri/lib/uri/wss.rb
new file mode 100644
index 00000000000000..3827053c7bd36c
--- /dev/null
+++ b/lib/bundler/vendor/uri/lib/uri/wss.rb
@@ -0,0 +1,22 @@
+# frozen_string_literal: false
+# = uri/wss.rb
+#
+# Author:: Matt Muller <mamuller@amazon.com>
+# License:: You can redistribute it and/or modify it under the same term as Ruby.
+#
+# See Bundler::URI for general documentation
+#
+
+require_relative 'ws'
+
+module Bundler::URI
+
+  # The default port for WSS URIs is 443, and the scheme is 'wss:' rather
+  # than 'ws:'. Other than that, WSS URIs are identical to WS URIs;
+  # see Bundler::URI::WS.
+  class WSS < WS
+    # A Default port of 443 for Bundler::URI::WSS
+    DEFAULT_PORT = 443
+  end
+  @@schemes['WSS'] = WSS
+end
diff --git a/lib/rubygems/exceptions.rb b/lib/rubygems/exceptions.rb
index 55755ddfba31cd..185efdb6ab58dc 100644
--- a/lib/rubygems/exceptions.rb
+++ b/lib/rubygems/exceptions.rb
@@ -225,7 +225,7 @@ class Gem::SystemExitException < SystemExit
   def initialize(exit_code)
     @exit_code = exit_code
 
-    super "Exiting RubyGems with exit_code #{exit_code}"
+    super exit_code, "Exiting RubyGems with exit_code #{exit_code}"
   end
 end
 
diff --git a/lib/rubygems/gemcutter_utilities.rb b/lib/rubygems/gemcutter_utilities.rb
index 00e68916c4202a..f4658810416eca 100644
--- a/lib/rubygems/gemcutter_utilities.rb
+++ b/lib/rubygems/gemcutter_utilities.rb
@@ -31,7 +31,8 @@ def add_key_option
 
   def add_otp_option
     add_option('--otp CODE',
-               'Digit code for multifactor authentication') do |value, options|
+               'Digit code for multifactor authentication',
+               'You can also use the environment variable GEM_HOST_OTP_CODE') do |value, options|
       options[:otp] = value
     end
   end
diff --git a/lib/rubygems/package/io_source.rb b/lib/rubygems/package/io_source.rb
index 7d7383110b93d3..03d7714524e584 100644
--- a/lib/rubygems/package/io_source.rb
+++ b/lib/rubygems/package/io_source.rb
@@ -32,10 +32,14 @@ def present?
 
   def with_read_io
     yield io
+  ensure
+    io.rewind
   end
 
   def with_write_io
     yield io
+  ensure
+    io.rewind
   end
 
   def path
diff --git a/spec/bundler/bundler/bundler_spec.rb b/spec/bundler/bundler/bundler_spec.rb
index 56ef4ce75ad46b..d164b5d3c69980 100644
--- a/spec/bundler/bundler/bundler_spec.rb
+++ b/spec/bundler/bundler/bundler_spec.rb
@@ -249,11 +249,8 @@
           allow(Bundler.rubygems).to receive(:user_home).and_return(path)
           allow(File).to receive(:directory?).with(path).and_return false
           allow(Bundler).to receive(:tmp).and_return(Pathname.new("/tmp/trulyrandom"))
-          message = <<EOF
-`/home/oggy` is not a directory.
-Bundler will use `/tmp/trulyrandom' as your home directory temporarily.
-EOF
-          expect(Bundler.ui).to receive(:warn).with(message)
+          expect(Bundler.ui).to receive(:warn).with("`/home/oggy` is not a directory.\n")
+          expect(Bundler.ui).to receive(:warn).with("Bundler will use `/tmp/trulyrandom' as your home directory temporarily.\n")
           expect(Bundler.user_home).to eq(Pathname("/tmp/trulyrandom"))
         end
       end
@@ -268,11 +265,8 @@
           allow(File).to receive(:writable?).with(path).and_return false
           allow(File).to receive(:directory?).with(dotbundle).and_return false
           allow(Bundler).to receive(:tmp).and_return(Pathname.new("/tmp/trulyrandom"))
-          message = <<EOF
-`/home/oggy` is not writable.
-Bundler will use `/tmp/trulyrandom' as your home directory temporarily.
-EOF
-          expect(Bundler.ui).to receive(:warn).with(message)
+          expect(Bundler.ui).to receive(:warn).with("`/home/oggy` is not writable.\n")
+          expect(Bundler.ui).to receive(:warn).with("Bundler will use `/tmp/trulyrandom' as your home directory temporarily.\n")
           expect(Bundler.user_home).to eq(Pathname("/tmp/trulyrandom"))
         end
 
@@ -293,11 +287,8 @@
       it "should issue warning and return a temporary user home" do
         allow(Bundler.rubygems).to receive(:user_home).and_return(nil)
         allow(Bundler).to receive(:tmp).and_return(Pathname.new("/tmp/trulyrandom"))
-        message = <<EOF
-Your home directory is not set.
-Bundler will use `/tmp/trulyrandom' as your home directory temporarily.
-EOF
-        expect(Bundler.ui).to receive(:warn).with(message)
+        expect(Bundler.ui).to receive(:warn).with("Your home directory is not set.\n")
+        expect(Bundler.ui).to receive(:warn).with("Bundler will use `/tmp/trulyrandom' as your home directory temporarily.\n")
         expect(Bundler.user_home).to eq(Pathname("/tmp/trulyrandom"))
       end
     end
diff --git a/spec/bundler/bundler/settings_spec.rb b/spec/bundler/bundler/settings_spec.rb
index 0f1a9c2a6f621b..24e3de7ba80c3b 100644
--- a/spec/bundler/bundler/settings_spec.rb
+++ b/spec/bundler/bundler/settings_spec.rb
@@ -64,13 +64,10 @@
 
   describe "#global_config_file" do
     context "when $HOME is not accessible" do
-      context "when $TMPDIR is not writable" do
-        it "does not raise" do
-          expect(Bundler.rubygems).to receive(:user_home).twice.and_return(nil)
-          expect(Bundler).to receive(:tmp).twice.and_raise(Errno::EROFS, "Read-only file system @ dir_s_mkdir - /tmp/bundler")
+      it "does not raise" do
+        expect(Bundler.rubygems).to receive(:user_home).twice.and_return(nil)
 
-          expect(subject.send(:global_config_file)).to be_nil
-        end
+        expect(subject.send(:global_config_file)).to be_nil
       end
     end
   end
diff --git a/spec/bundler/commands/check_spec.rb b/spec/bundler/commands/check_spec.rb
index 2860c82a123e00..88950cef852959 100644
--- a/spec/bundler/commands/check_spec.rb
+++ b/spec/bundler/commands/check_spec.rb
@@ -288,6 +288,34 @@
     end
   end
 
+  describe "when locked with multiple dependents with different requirements" do
+    before :each do
+      build_repo4 do
+        build_gem "depends_on_rack" do |s|
+          s.add_dependency "rack", ">= 1.0"
+        end
+        build_gem "also_depends_on_rack" do |s|
+          s.add_dependency "rack", "~> 1.0"
+        end
+        build_gem "rack"
+      end
+
+      gemfile <<-G
+        source "#{file_uri_for(gem_repo4)}"
+        gem "depends_on_rack"
+        gem "also_depends_on_rack"
+      G
+
+      bundle "lock"
+    end
+
+    it "shows what is missing with the current Gemfile without duplications" do
+      bundle :check, :raise_on_error => false
+      expect(err).to match(/The following gems are missing/)
+      expect(err).to include("* rack (1.0").once
+    end
+  end
+
   describe "when using only scoped rubygems sources" do
     before do
       gemfile <<~G
diff --git a/spec/bundler/commands/exec_spec.rb b/spec/bundler/commands/exec_spec.rb
index 0d104ad30456dc..39430d52a4987d 100644
--- a/spec/bundler/commands/exec_spec.rb
+++ b/spec/bundler/commands/exec_spec.rb
@@ -24,6 +24,16 @@
     expect(out).to eq("0.9.1")
   end
 
+  it "works and prints no warnings when HOME is not writable" do
+    gemfile <<-G
+      gem "rack", "0.9.1"
+    G
+
+    bundle "exec rackup", :env => { "HOME" => "/" }
+    expect(out).to eq("0.9.1")
+    expect(err).to be_empty
+  end
+
   it "works when the bins are in ~/.bundle" do
     install_gemfile <<-G
       gem "rack"
diff --git a/spec/bundler/commands/install_spec.rb b/spec/bundler/commands/install_spec.rb
index c91864dbb82f3e..3c0c35d84484a6 100644
--- a/spec/bundler/commands/install_spec.rb
+++ b/spec/bundler/commands/install_spec.rb
@@ -344,54 +344,72 @@
       expect(File.exist?(bundled_app_lock)).to eq(true)
     end
 
-    context "throws a warning if a gem is added twice in Gemfile" do
-      it "without version requirements" do
-        install_gemfile <<-G, :raise_on_error => false
-          source "#{file_uri_for(gem_repo2)}"
-          gem "rack"
-          gem "rack"
-        G
+    it "throws a warning if a gem is added twice in Gemfile without version requirements" do
+      install_gemfile <<-G, :raise_on_error => false
+        source "#{file_uri_for(gem_repo2)}"
+        gem "rack"
+        gem "rack"
+      G
 
-        expect(err).to include("Your Gemfile lists the gem rack (>= 0) more than once.")
-        expect(err).to include("Remove any duplicate entries and specify the gem only once.")
-        expect(err).to include("While it's not a problem now, it could cause errors if you change the version of one of them later.")
-      end
+      expect(err).to include("Your Gemfile lists the gem rack (>= 0) more than once.")
+      expect(err).to include("Remove any duplicate entries and specify the gem only once.")
+      expect(err).to include("While it's not a problem now, it could cause errors if you change the version of one of them later.")
+    end
 
-      it "with same versions" do
-        install_gemfile <<-G, :raise_on_error => false
-          source "#{file_uri_for(gem_repo2)}"
-          gem "rack", "1.0"
-          gem "rack", "1.0"
-        G
+    it "throws a warning if a gem is added twice in Gemfile with same versions" do
+      install_gemfile <<-G, :raise_on_error => false
+        source "#{file_uri_for(gem_repo2)}"
+        gem "rack", "1.0"
+        gem "rack", "1.0"
+      G
 
-        expect(err).to include("Your Gemfile lists the gem rack (= 1.0) more than once.")
-        expect(err).to include("Remove any duplicate entries and specify the gem only once.")
-        expect(err).to include("While it's not a problem now, it could cause errors if you change the version of one of them later.")
-      end
+      expect(err).to include("Your Gemfile lists the gem rack (= 1.0) more than once.")
+      expect(err).to include("Remove any duplicate entries and specify the gem only once.")
+      expect(err).to include("While it's not a problem now, it could cause errors if you change the version of one of them later.")
     end
 
-    context "throws an error if a gem is added twice in Gemfile" do
-      it "when version of one dependency is not specified" do
-        install_gemfile <<-G, :raise_on_error => false
-          source "#{file_uri_for(gem_repo2)}"
-          gem "rack"
-          gem "rack", "1.0"
-        G
+    it "does not throw a warning if a gem is added once in Gemfile and also inside a gemspec as a development dependency" do
+      build_lib "my-gem", :path => bundled_app do |s|
+        s.add_development_dependency "my-private-gem"
+      end
 
-        expect(err).to include("You cannot specify the same gem twice with different version requirements")
-        expect(err).to include("You specified: rack (>= 0) and rack (= 1.0).")
+      build_repo2 do
+        build_gem "my-private-gem"
       end
 
-      it "when different versions of both dependencies are specified" do
-        install_gemfile <<-G, :raise_on_error => false
-          source "#{file_uri_for(gem_repo2)}"
-          gem "rack", "1.0"
-          gem "rack", "1.1"
-        G
+      gemfile <<~G
+        source "#{file_uri_for(gem_repo2)}"
 
-        expect(err).to include("You cannot specify the same gem twice with different version requirements")
-        expect(err).to include("You specified: rack (= 1.0) and rack (= 1.1).")
-      end
+        gemspec
+
+        gem "my-private-gem", :group => :development
+      G
+
+      bundle :install
+
+      expect(err).to be_empty
+    end
+
+    it "throws an error if a gem is added twice in Gemfile when version of one dependency is not specified" do
+      install_gemfile <<-G, :raise_on_error => false
+        source "#{file_uri_for(gem_repo2)}"
+        gem "rack"
+        gem "rack", "1.0"
+      G
+
+      expect(err).to include("You cannot specify the same gem twice with different version requirements")
+      expect(err).to include("You specified: rack (>= 0) and rack (= 1.0).")
+    end
+
+    it "throws an error if a gem is added twice in Gemfile when different versions of both dependencies are specified" do
+      install_gemfile <<-G, :raise_on_error => false
+        source "#{file_uri_for(gem_repo2)}"
+        gem "rack", "1.0"
+        gem "rack", "1.1"
+      G
+
+      expect(err).to include("You cannot specify the same gem twice with different version requirements")
+      expect(err).to include("You specified: rack (= 1.0) and rack (= 1.1).")
     end
 
     it "gracefully handles error when rubygems server is unavailable" do
diff --git a/spec/bundler/commands/newgem_spec.rb b/spec/bundler/commands/newgem_spec.rb
index 00bd009c5a8403..56fea008eccf15 100644
--- a/spec/bundler/commands/newgem_spec.rb
+++ b/spec/bundler/commands/newgem_spec.rb
@@ -307,42 +307,42 @@ def bundle_exec_standardrb
     skip "ruby_core has an 'ast.rb' file that gets in the middle and breaks this spec" if ruby_core?
     bundle "gem #{gem_name} --linter=rubocop"
     bundle_exec_rubocop
-    expect(err).to be_empty
+    expect(last_command).to be_success
   end
 
   it "has no rubocop offenses when using --ext and --linter=rubocop flag", :readline do
     skip "ruby_core has an 'ast.rb' file that gets in the middle and breaks this spec" if ruby_core?
     bundle "gem #{gem_name} --ext --linter=rubocop"
     bundle_exec_rubocop
-    expect(err).to be_empty
+    expect(last_command).to be_success
   end
 
   it "has no rubocop offenses when using --ext, --test=minitest, and --linter=rubocop flag", :readline do
     skip "ruby_core has an 'ast.rb' file that gets in the middle and breaks this spec" if ruby_core?
     bundle "gem #{gem_name} --ext --test=minitest --linter=rubocop"
     bundle_exec_rubocop
-    expect(err).to be_empty
+    expect(last_command).to be_success
   end
 
   it "has no rubocop offenses when using --ext, --test=rspec, and --linter=rubocop flag", :readline do
     skip "ruby_core has an 'ast.rb' file that gets in the middle and breaks this spec" if ruby_core?
     bundle "gem #{gem_name} --ext --test=rspec --linter=rubocop"
     bundle_exec_rubocop
-    expect(err).to be_empty
+    expect(last_command).to be_success
   end
 
   it "has no rubocop offenses when using --ext, --ext=test-unit, and --linter=rubocop flag", :readline do
     skip "ruby_core has an 'ast.rb' file that gets in the middle and breaks this spec" if ruby_core?
     bundle "gem #{gem_name} --ext --test=test-unit --linter=rubocop"
     bundle_exec_rubocop
-    expect(err).to be_empty
+    expect(last_command).to be_success
   end
 
   it "has no standard offenses when using --linter=standard flag", :readline do
     skip "ruby_core has an 'ast.rb' file that gets in the middle and breaks this spec" if ruby_core?
     bundle "gem #{gem_name} --linter=standard"
     bundle_exec_standardrb
-    expect(err).to be_empty
+    expect(last_command).to be_success
   end
 
   shared_examples_for "CI config is absent" do
diff --git a/spec/bundler/install/gemfile/specific_platform_spec.rb b/spec/bundler/install/gemfile/specific_platform_spec.rb
index c6e526a95ed1f2..a6d8318fe4b66e 100644
--- a/spec/bundler/install/gemfile/specific_platform_spec.rb
+++ b/spec/bundler/install/gemfile/specific_platform_spec.rb
@@ -249,6 +249,38 @@
     end
   end
 
+  it "installs sorbet-static, which does not provide a pure ruby variant, just fine on truffleruby", :truffleruby do
+    build_repo2 do
+      build_gem("sorbet-static", "0.5.6403") {|s| s.platform = "x86_64-linux" }
+      build_gem("sorbet-static", "0.5.6403") {|s| s.platform = "universal-darwin-20" }
+    end
+
+    gemfile <<~G
+      source "#{file_uri_for(gem_repo2)}"
+
+      gem "sorbet-static", "0.5.6403"
+    G
+
+    lockfile <<~L
+      GEM
+        remote: #{file_uri_for(gem_repo2)}/
+        specs:
+          sorbet-static (0.5.6403-universal-darwin-20)
+          sorbet-static (0.5.6403-x86_64-linux)
+
+      PLATFORMS
+        ruby
+
+      DEPENDENCIES
+        sorbet-static (= 0.5.6403)
+
+      BUNDLED WITH
+         #{Bundler::VERSION}
+    L
+
+    bundle "install --verbose"
+  end
+
   private
 
   def setup_multiplatform_gem
diff --git a/spec/bundler/plugins/install_spec.rb b/spec/bundler/plugins/install_spec.rb
index 308f9c79fc3a22..2175610b103182 100644
--- a/spec/bundler/plugins/install_spec.rb
+++ b/spec/bundler/plugins/install_spec.rb
@@ -22,6 +22,13 @@
     plugin_should_be_installed("foo")
   end
 
+  it "installs from sources configured as Gem.sources without any flags" do
+    bundle "plugin install foo", :env => { "BUNDLER_SPEC_GEM_SOURCES" => file_uri_for(gem_repo2).to_s }
+
+    expect(out).to include("Installed plugin foo")
+    plugin_should_be_installed("foo")
+  end
+
   context "plugin is already installed" do
     before do
       bundle "plugin install foo --source #{file_uri_for(gem_repo2)}"
diff --git a/spec/bundler/realworld/edgecases_spec.rb b/spec/bundler/realworld/edgecases_spec.rb
index 556a11d2f32947..f031e2f354a67e 100644
--- a/spec/bundler/realworld/edgecases_spec.rb
+++ b/spec/bundler/realworld/edgecases_spec.rb
@@ -196,21 +196,6 @@ def rubygems_version(name, requirement)
     expect(lockfile).to include(rubygems_version("paperclip", "~> 5.1.0"))
   end
 
-  # https://github.com/rubygems/bundler/issues/1500
-  it "does not fail install because of gem plugins" do
-    realworld_system_gems("open_gem --version 1.4.2", "rake --version 0.9.2")
-    gemfile <<-G
-      source "https://rubygems.org"
-
-      gem 'rack', '1.0.1'
-    G
-
-    bundle "config set --local path vendor/bundle"
-    bundle :install
-    expect(err).not_to include("Could not find rake")
-    expect(err).to be_empty
-  end
-
   it "outputs a helpful error message when gems have invalid gemspecs" do
     install_gemfile <<-G, :standalone => true, :raise_on_error => false
       source 'https://rubygems.org'
diff --git a/spec/bundler/runtime/setup_spec.rb b/spec/bundler/runtime/setup_spec.rb
index d8ba569f0abb96..380db991364d53 100644
--- a/spec/bundler/runtime/setup_spec.rb
+++ b/spec/bundler/runtime/setup_spec.rb
@@ -644,6 +644,25 @@ def clean_load_path(lp)
       expect(err).to be_empty
     end
 
+    it "doesn't re-resolve when a pre-release bundler is used and a dependency includes a dependency on bundler" do
+      system_gems "bundler-9.99.9.beta1"
+
+      build_repo4 do
+        build_gem "depends_on_bundler", "1.0" do |s|
+          s.add_dependency "bundler", ">= 1.5.0"
+        end
+      end
+
+      install_gemfile <<~G
+        source "#{file_uri_for(gem_repo4)}"
+        gem "depends_on_bundler"
+      G
+
+      ruby "require '#{system_gem_path("gems/bundler-9.99.9.beta1/lib/bundler.rb")}'; Bundler.setup", :env => { "DEBUG" => "1" }
+      expect(out).to include("Found no changes, using resolution from the lockfile")
+      expect(err).to be_empty
+    end
+
     it "remembers --without and does not include groups passed to Bundler.setup" do
       bundle "config set --local without rails"
       install_gemfile <<-G
diff --git a/spec/bundler/support/artifice/vcr.rb b/spec/bundler/support/artifice/vcr.rb
index 88c33d93dcac5b..0d51201bef837a 100644
--- a/spec/bundler/support/artifice/vcr.rb
+++ b/spec/bundler/support/artifice/vcr.rb
@@ -133,6 +133,19 @@ def binwrite(path, contents)
     end
   end
 
+  def start_with_vcr
+    if ENV["BUNDLER_SPEC_PRE_RECORDED"]
+      raise IOError, "HTTP session already opened" if @started
+      @socket = nil
+      @started = true
+    else
+      start_without_vcr
+    end
+  end
+
+  alias_method :start_without_vcr, :start
+  alias_method :start, :start_with_vcr
+
   def request_with_vcr(request, *args, &block)
     handler = request.instance_eval do
       remove_instance_variable(:@__vcr_request_handler) if defined?(@__vcr_request_handler)
diff --git a/spec/bundler/support/hax.rb b/spec/bundler/support/hax.rb
index ddb62f7d531162..aaf8c748940251 100644
--- a/spec/bundler/support/hax.rb
+++ b/spec/bundler/support/hax.rb
@@ -28,6 +28,10 @@ def finish_resolve
     end
   end
 
+  if ENV["BUNDLER_SPEC_GEM_SOURCES"]
+    @sources = [ENV["BUNDLER_SPEC_GEM_SOURCES"]]
+  end
+
   # We only need this hack for rubygems versions without the BundlerVersionFinder
   if Gem.rubygems_version < Gem::Version.new("2.7.0")
     @path_to_default_spec_map.delete_if do |_path, spec|
diff --git a/test/rubygems/test_exit.rb b/test/rubygems/test_exit.rb
new file mode 100644
index 00000000000000..9557fe5d063131
--- /dev/null
+++ b/test/rubygems/test_exit.rb
@@ -0,0 +1,11 @@
+# frozen_string_literal: true
+
+require_relative 'helper'
+require 'rubygems'
+
+class TestExit < Gem::TestCase
+  def test_exit
+    system(*ruby_with_rubygems_in_load_path, "-e", "raise Gem::SystemExitException.new(2)")
+    assert_equal 2, $?.exitstatus
+  end
+end
diff --git a/test/rubygems/test_gem_package.rb b/test/rubygems/test_gem_package.rb
index dbb037fd80ed91..3fa2c1911c45ef 100644
--- a/test/rubygems/test_gem_package.rb
+++ b/test/rubygems/test_gem_package.rb
@@ -1145,6 +1145,13 @@ def test_spec_from_io_raises_gem_error_for_io_not_at_start
     end
   end
 
+  def test_contents_from_io
+    io = StringIO.new Gem.read_binary @gem
+    package = Gem::Package.new io
+
+    assert_equal %w[lib/code.rb], package.contents
+  end
+
   def util_tar
     tar_io = StringIO.new