diff --git a/lib/rubygems.rb b/lib/rubygems.rb
index 9e8776b027d9c4..80708e2aa00c4d 100644
--- a/lib/rubygems.rb
+++ b/lib/rubygems.rb
@@ -12,11 +12,11 @@ module Gem
 end
 
 # Must be first since it unloads the prelude from 1.9.2
-require 'rubygems/compatibility'
+require_relative 'rubygems/compatibility'
 
-require 'rubygems/defaults'
-require 'rubygems/deprecate'
-require 'rubygems/errors'
+require_relative 'rubygems/defaults'
+require_relative 'rubygems/deprecate'
+require_relative 'rubygems/errors'
 
 ##
 # RubyGems is the Ruby standard for publishing and managing third party
@@ -559,7 +559,7 @@ def self.find_latest_files(glob, check_load_path=true)
   #   => [#<Gem::Specification:0x1013b4528 @name="minitest", ...>]
 
   def self.install(name, version = Gem::Requirement.default, *options)
-    require "rubygems/dependency_installer"
+    require_relative "rubygems/dependency_installer"
     inst = Gem::DependencyInstaller.new(*options)
     inst.install name, version
     inst.installed_gems
@@ -625,12 +625,12 @@ def self.load_yaml
     rescue ::LoadError
       # If we can't load psych, that's fine, go on.
     else
-      require 'rubygems/psych_additions'
-      require 'rubygems/psych_tree'
+      require_relative 'rubygems/psych_additions'
+      require_relative 'rubygems/psych_tree'
     end
 
     require 'yaml'
-    require 'rubygems/safe_yaml'
+    require_relative 'rubygems/safe_yaml'
 
     @yaml_loaded = true
   end
@@ -990,7 +990,7 @@ def self.time(msg, width = 0, display = Gem.configuration.verbose)
   # Lazily loads DefaultUserInteraction and returns the default UI.
 
   def self.ui
-    require 'rubygems/user_interaction'
+    require_relative 'rubygems/user_interaction'
 
     Gem::DefaultUserInteraction.ui
   end
@@ -1110,7 +1110,7 @@ def self.use_gemdeps(path = nil)
     end
 
     ENV["BUNDLE_GEMFILE"] ||= File.expand_path(path)
-    require 'rubygems/user_interaction'
+    require_relative 'rubygems/user_interaction'
     require "bundler"
     begin
       Gem::DefaultUserInteraction.use_ui(ui) do
@@ -1322,7 +1322,7 @@ def default_gem_load_paths
   autoload :Version,            File.expand_path('rubygems/version', __dir__)
 end
 
-require 'rubygems/exceptions'
+require_relative 'rubygems/exceptions'
 
 # REFACTOR: This should be pulled out into some kind of hacks file.
 begin
@@ -1353,6 +1353,6 @@ def default_gem_load_paths
 # Loads the default specs.
 Gem::Specification.load_defaults
 
-require 'rubygems/core_ext/kernel_gem'
-require 'rubygems/core_ext/kernel_require'
-require 'rubygems/core_ext/kernel_warn'
+require_relative 'rubygems/core_ext/kernel_gem'
+require_relative 'rubygems/core_ext/kernel_require'
+require_relative 'rubygems/core_ext/kernel_warn'
diff --git a/lib/rubygems/command_manager.rb b/lib/rubygems/command_manager.rb
index 2409550882718d..39bf8bd30d1c99 100644
--- a/lib/rubygems/command_manager.rb
+++ b/lib/rubygems/command_manager.rb
@@ -5,9 +5,9 @@
 # See LICENSE.txt for permissions.
 #++
 
-require 'rubygems/command'
-require 'rubygems/user_interaction'
-require 'rubygems/text'
+require_relative 'command'
+require_relative 'user_interaction'
+require_relative 'text'
 
 ##
 # The command manager registers and installs all the individual sub-commands
diff --git a/lib/rubygems/commands/build_command.rb b/lib/rubygems/commands/build_command.rb
index 842ec1855a6873..6d1a057dfa7303 100644
--- a/lib/rubygems/commands/build_command.rb
+++ b/lib/rubygems/commands/build_command.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/package'
-require 'rubygems/version_option'
+require_relative '../command'
+require_relative '../package'
+require_relative '../version_option'
 
 class Gem::Commands::BuildCommand < Gem::Command
   include Gem::VersionOption
diff --git a/lib/rubygems/commands/cert_command.rb b/lib/rubygems/commands/cert_command.rb
index 3fc0daea7d8dae..bdfeb0ba6e84f7 100644
--- a/lib/rubygems/commands/cert_command.rb
+++ b/lib/rubygems/commands/cert_command.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/security'
+require_relative '../command'
+require_relative '../security'
 
 class Gem::Commands::CertCommand < Gem::Command
   def initialize
diff --git a/lib/rubygems/commands/check_command.rb b/lib/rubygems/commands/check_command.rb
index 8b8eda53cf7411..3b6b97ae3bf53c 100644
--- a/lib/rubygems/commands/check_command.rb
+++ b/lib/rubygems/commands/check_command.rb
@@ -1,8 +1,8 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/version_option'
-require 'rubygems/validator'
-require 'rubygems/doctor'
+require_relative '../command'
+require_relative '../version_option'
+require_relative '../validator'
+require_relative '../doctor'
 
 class Gem::Commands::CheckCommand < Gem::Command
   include Gem::VersionOption
diff --git a/lib/rubygems/commands/cleanup_command.rb b/lib/rubygems/commands/cleanup_command.rb
index 662badce33ac49..c965085880ff84 100644
--- a/lib/rubygems/commands/cleanup_command.rb
+++ b/lib/rubygems/commands/cleanup_command.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/dependency_list'
-require 'rubygems/uninstaller'
+require_relative '../command'
+require_relative '../dependency_list'
+require_relative '../uninstaller'
 
 class Gem::Commands::CleanupCommand < Gem::Command
   def initialize
diff --git a/lib/rubygems/commands/contents_command.rb b/lib/rubygems/commands/contents_command.rb
index f17aed64db1bf4..716022c458232b 100644
--- a/lib/rubygems/commands/contents_command.rb
+++ b/lib/rubygems/commands/contents_command.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/version_option'
+require_relative '../command'
+require_relative '../version_option'
 
 class Gem::Commands::ContentsCommand < Gem::Command
   include Gem::VersionOption
diff --git a/lib/rubygems/commands/dependency_command.rb b/lib/rubygems/commands/dependency_command.rb
index e472d8fa8daf2b..7d217076a57b08 100644
--- a/lib/rubygems/commands/dependency_command.rb
+++ b/lib/rubygems/commands/dependency_command.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/local_remote_options'
-require 'rubygems/version_option'
+require_relative '../command'
+require_relative '../local_remote_options'
+require_relative '../version_option'
 
 class Gem::Commands::DependencyCommand < Gem::Command
   include Gem::LocalRemoteOptions
diff --git a/lib/rubygems/commands/environment_command.rb b/lib/rubygems/commands/environment_command.rb
index 37429fb836ac0f..b6eeb620bdc3c3 100644
--- a/lib/rubygems/commands/environment_command.rb
+++ b/lib/rubygems/commands/environment_command.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require 'rubygems/command'
+require_relative '../command'
 
 class Gem::Commands::EnvironmentCommand < Gem::Command
   def initialize
diff --git a/lib/rubygems/commands/fetch_command.rb b/lib/rubygems/commands/fetch_command.rb
index 6a1b346dd3e1f1..619f56a5da60e7 100644
--- a/lib/rubygems/commands/fetch_command.rb
+++ b/lib/rubygems/commands/fetch_command.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/local_remote_options'
-require 'rubygems/version_option'
+require_relative '../command'
+require_relative '../local_remote_options'
+require_relative '../version_option'
 
 class Gem::Commands::FetchCommand < Gem::Command
   include Gem::LocalRemoteOptions
diff --git a/lib/rubygems/commands/generate_index_command.rb b/lib/rubygems/commands/generate_index_command.rb
index 93e25ef5e4df8a..87200dab91dbbe 100644
--- a/lib/rubygems/commands/generate_index_command.rb
+++ b/lib/rubygems/commands/generate_index_command.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/indexer'
+require_relative '../command'
+require_relative '../indexer'
 
 ##
 # Generates a index files for use as a gem server.
diff --git a/lib/rubygems/commands/help_command.rb b/lib/rubygems/commands/help_command.rb
index 4e8d7600fb9552..7f3383c9f3007a 100644
--- a/lib/rubygems/commands/help_command.rb
+++ b/lib/rubygems/commands/help_command.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require 'rubygems/command'
+require_relative '../command'
 
 class Gem::Commands::HelpCommand < Gem::Command
   # :stopdoc:
diff --git a/lib/rubygems/commands/info_command.rb b/lib/rubygems/commands/info_command.rb
index 9ca6ae364fae75..3f2dd4ae0bda32 100644
--- a/lib/rubygems/commands/info_command.rb
+++ b/lib/rubygems/commands/info_command.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
 
-require 'rubygems/command'
-require 'rubygems/query_utils'
+require_relative '../command'
+require_relative '../query_utils'
 
 class Gem::Commands::InfoCommand < Gem::Command
   include Gem::QueryUtils
diff --git a/lib/rubygems/commands/install_command.rb b/lib/rubygems/commands/install_command.rb
index 4d36c69d510dff..92430ea444d23e 100644
--- a/lib/rubygems/commands/install_command.rb
+++ b/lib/rubygems/commands/install_command.rb
@@ -1,10 +1,10 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/install_update_options'
-require 'rubygems/dependency_installer'
-require 'rubygems/local_remote_options'
-require 'rubygems/validator'
-require 'rubygems/version_option'
+require_relative '../command'
+require_relative '../install_update_options'
+require_relative '../dependency_installer'
+require_relative '../local_remote_options'
+require_relative '../validator'
+require_relative '../version_option'
 
 ##
 # Gem installer command line tool
@@ -172,7 +172,7 @@ def execute
   end
 
   def install_from_gemdeps # :nodoc:
-    require 'rubygems/request_set'
+    require_relative '../request_set'
     rs = Gem::RequestSet.new
 
     specs = rs.install_from_gemdeps options do |req, inst|
@@ -247,11 +247,11 @@ def install_gems # :nodoc:
 
   def load_hooks # :nodoc:
     if options[:install_as_default]
-      require 'rubygems/install_default_message'
+      require_relative '../install_default_message'
     else
-      require 'rubygems/install_message'
+      require_relative '../install_message'
     end
-    require 'rubygems/rdoc'
+    require_relative '../rdoc'
   end
 
   def show_install_errors(errors) # :nodoc:
diff --git a/lib/rubygems/commands/list_command.rb b/lib/rubygems/commands/list_command.rb
index 5c99d3d73d72a5..dea11111c96872 100644
--- a/lib/rubygems/commands/list_command.rb
+++ b/lib/rubygems/commands/list_command.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/query_utils'
+require_relative '../command'
+require_relative '../query_utils'
 
 ##
 # Searches for gems starting with the supplied argument.
diff --git a/lib/rubygems/commands/lock_command.rb b/lib/rubygems/commands/lock_command.rb
index f1dc1ac586f3a5..cb6229a2cbc8ce 100644
--- a/lib/rubygems/commands/lock_command.rb
+++ b/lib/rubygems/commands/lock_command.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require 'rubygems/command'
+require_relative '../command'
 
 class Gem::Commands::LockCommand < Gem::Command
   def initialize
diff --git a/lib/rubygems/commands/mirror_command.rb b/lib/rubygems/commands/mirror_command.rb
index 86671a93b27fbc..7daa47e2f0ad6a 100644
--- a/lib/rubygems/commands/mirror_command.rb
+++ b/lib/rubygems/commands/mirror_command.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require 'rubygems/command'
+require_relative '../command'
 
 unless defined? Gem::Commands::MirrorCommand
   class Gem::Commands::MirrorCommand < Gem::Command
diff --git a/lib/rubygems/commands/open_command.rb b/lib/rubygems/commands/open_command.rb
index 8012a9a0e1a320..1e616fd68f3f86 100644
--- a/lib/rubygems/commands/open_command.rb
+++ b/lib/rubygems/commands/open_command.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/version_option'
+require_relative '../command'
+require_relative '../version_option'
 
 class Gem::Commands::OpenCommand < Gem::Command
   include Gem::VersionOption
diff --git a/lib/rubygems/commands/outdated_command.rb b/lib/rubygems/commands/outdated_command.rb
index 3579bfc3ba5c24..162d3383201ddf 100644
--- a/lib/rubygems/commands/outdated_command.rb
+++ b/lib/rubygems/commands/outdated_command.rb
@@ -1,8 +1,8 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/local_remote_options'
-require 'rubygems/spec_fetcher'
-require 'rubygems/version_option'
+require_relative '../command'
+require_relative '../local_remote_options'
+require_relative '../spec_fetcher'
+require_relative '../version_option'
 
 class Gem::Commands::OutdatedCommand < Gem::Command
   include Gem::LocalRemoteOptions
diff --git a/lib/rubygems/commands/owner_command.rb b/lib/rubygems/commands/owner_command.rb
index dd490274695c31..0a5665228f6fd4 100644
--- a/lib/rubygems/commands/owner_command.rb
+++ b/lib/rubygems/commands/owner_command.rb
@@ -1,8 +1,8 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/local_remote_options'
-require 'rubygems/gemcutter_utilities'
-require 'rubygems/text'
+require_relative '../command'
+require_relative '../local_remote_options'
+require_relative '../gemcutter_utilities'
+require_relative '../text'
 
 class Gem::Commands::OwnerCommand < Gem::Command
   include Gem::Text
diff --git a/lib/rubygems/commands/pristine_command.rb b/lib/rubygems/commands/pristine_command.rb
index 143105981e1aa4..41547ce73bfedc 100644
--- a/lib/rubygems/commands/pristine_command.rb
+++ b/lib/rubygems/commands/pristine_command.rb
@@ -1,8 +1,8 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/package'
-require 'rubygems/installer'
-require 'rubygems/version_option'
+require_relative '../command'
+require_relative '../package'
+require_relative '../installer'
+require_relative '../version_option'
 
 class Gem::Commands::PristineCommand < Gem::Command
   include Gem::VersionOption
@@ -138,7 +138,7 @@ def execute
       gem = spec.cache_file
 
       unless File.exist? gem or options[:only_executables] or options[:only_plugins]
-        require 'rubygems/remote_fetcher'
+        require_relative '../remote_fetcher'
 
         say "Cached gem for #{spec.full_name} not found, attempting to fetch..."
 
diff --git a/lib/rubygems/commands/push_command.rb b/lib/rubygems/commands/push_command.rb
index 1a9a1932f85d2c..1864b4b09578db 100644
--- a/lib/rubygems/commands/push_command.rb
+++ b/lib/rubygems/commands/push_command.rb
@@ -1,8 +1,8 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/local_remote_options'
-require 'rubygems/gemcutter_utilities'
-require 'rubygems/package'
+require_relative '../command'
+require_relative '../local_remote_options'
+require_relative '../gemcutter_utilities'
+require_relative '../package'
 
 class Gem::Commands::PushCommand < Gem::Command
   include Gem::LocalRemoteOptions
diff --git a/lib/rubygems/commands/query_command.rb b/lib/rubygems/commands/query_command.rb
index 789afd65093086..5896bec44e6a6b 100644
--- a/lib/rubygems/commands/query_command.rb
+++ b/lib/rubygems/commands/query_command.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/query_utils'
-require 'rubygems/deprecate'
+require_relative '../command'
+require_relative '../query_utils'
+require_relative '../deprecate'
 
 class Gem::Commands::QueryCommand < Gem::Command
   extend Gem::Deprecate
diff --git a/lib/rubygems/commands/rdoc_command.rb b/lib/rubygems/commands/rdoc_command.rb
index e8c9e84b29f7d9..305c80ccfef9ce 100644
--- a/lib/rubygems/commands/rdoc_command.rb
+++ b/lib/rubygems/commands/rdoc_command.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/version_option'
-require 'rubygems/rdoc'
+require_relative '../command'
+require_relative '../version_option'
+require_relative '../rdoc'
 require 'fileutils'
 
 class Gem::Commands::RdocCommand < Gem::Command
diff --git a/lib/rubygems/commands/search_command.rb b/lib/rubygems/commands/search_command.rb
index aeb2119235d0ea..488d7779391da4 100644
--- a/lib/rubygems/commands/search_command.rb
+++ b/lib/rubygems/commands/search_command.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/query_utils'
+require_relative '../command'
+require_relative '../query_utils'
 
 class Gem::Commands::SearchCommand < Gem::Command
   include Gem::QueryUtils
diff --git a/lib/rubygems/commands/server_command.rb b/lib/rubygems/commands/server_command.rb
index 594cf77f662e4a..f3c08efb5eba30 100644
--- a/lib/rubygems/commands/server_command.rb
+++ b/lib/rubygems/commands/server_command.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/server'
-require 'rubygems/deprecate'
+require_relative '../command'
+require_relative '../server'
+require_relative '../deprecate'
 
 class Gem::Commands::ServerCommand < Gem::Command
   extend Gem::Deprecate
diff --git a/lib/rubygems/commands/setup_command.rb b/lib/rubygems/commands/setup_command.rb
index 8b1098f63f2f96..edb3498eec10ed 100644
--- a/lib/rubygems/commands/setup_command.rb
+++ b/lib/rubygems/commands/setup_command.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require 'rubygems/command'
+require_relative '../command'
 
 ##
 # Installs RubyGems itself.  This command is ordinarily only available from a
@@ -348,7 +348,7 @@ def install_rdoc
         rm_rf dir
       end
 
-      require 'rubygems/rdoc'
+      require_relative '../rdoc'
 
       fake_spec = Gem::Specification.new 'rubygems', Gem::VERSION
       def fake_spec.full_gem_path
@@ -407,7 +407,7 @@ def install_default_bundler_gem(bin_dir)
       cp File.join("bundler", bundler_spec.bindir, e), File.join(bundler_bin_dir, e)
     end
 
-    require 'rubygems/installer'
+    require_relative '../installer'
 
     Dir.chdir("bundler") do
       built_gem = Gem::Package.build(bundler_spec)
@@ -584,7 +584,7 @@ def show_release_notes
   end
 
   def uninstall_old_gemcutter
-    require 'rubygems/uninstaller'
+    require_relative '../uninstaller'
 
     ui = Gem::Uninstaller.new('gemcutter', :all => true, :ignore => true,
                               :version => '< 0.4')
@@ -593,7 +593,7 @@ def uninstall_old_gemcutter
   end
 
   def regenerate_binstubs
-    require "rubygems/commands/pristine_command"
+    require_relative "pristine_command"
     say "Regenerating binstubs"
 
     args = %w[--all --only-executables --silent]
diff --git a/lib/rubygems/commands/signin_command.rb b/lib/rubygems/commands/signin_command.rb
index 2e19c8333c47ff..23bb2f937fc820 100644
--- a/lib/rubygems/commands/signin_command.rb
+++ b/lib/rubygems/commands/signin_command.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/gemcutter_utilities'
+require_relative '../command'
+require_relative '../gemcutter_utilities'
 
 class Gem::Commands::SigninCommand < Gem::Command
   include Gem::GemcutterUtilities
diff --git a/lib/rubygems/commands/signout_command.rb b/lib/rubygems/commands/signout_command.rb
index ebbe746cb47536..c9485e0c1b4488 100644
--- a/lib/rubygems/commands/signout_command.rb
+++ b/lib/rubygems/commands/signout_command.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require 'rubygems/command'
+require_relative '../command'
 
 class Gem::Commands::SignoutCommand < Gem::Command
   def initialize
diff --git a/lib/rubygems/commands/sources_command.rb b/lib/rubygems/commands/sources_command.rb
index f74fb12e428fa8..9e74f3c47dfa05 100644
--- a/lib/rubygems/commands/sources_command.rb
+++ b/lib/rubygems/commands/sources_command.rb
@@ -1,8 +1,8 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/remote_fetcher'
-require 'rubygems/spec_fetcher'
-require 'rubygems/local_remote_options'
+require_relative '../command'
+require_relative '../remote_fetcher'
+require_relative '../spec_fetcher'
+require_relative '../local_remote_options'
 
 class Gem::Commands::SourcesCommand < Gem::Command
   include Gem::LocalRemoteOptions
diff --git a/lib/rubygems/commands/specification_command.rb b/lib/rubygems/commands/specification_command.rb
index 3fddaaaf302640..473b6e7b198508 100644
--- a/lib/rubygems/commands/specification_command.rb
+++ b/lib/rubygems/commands/specification_command.rb
@@ -1,8 +1,8 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/local_remote_options'
-require 'rubygems/version_option'
-require 'rubygems/package'
+require_relative '../command'
+require_relative '../local_remote_options'
+require_relative '../version_option'
+require_relative '../package'
 
 class Gem::Commands::SpecificationCommand < Gem::Command
   include Gem::LocalRemoteOptions
diff --git a/lib/rubygems/commands/stale_command.rb b/lib/rubygems/commands/stale_command.rb
index badc9905c124b5..62a97966f1f7d7 100644
--- a/lib/rubygems/commands/stale_command.rb
+++ b/lib/rubygems/commands/stale_command.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require 'rubygems/command'
+require_relative '../command'
 
 class Gem::Commands::StaleCommand < Gem::Command
   def initialize
diff --git a/lib/rubygems/commands/uninstall_command.rb b/lib/rubygems/commands/uninstall_command.rb
index 1540b2f0fb8e14..20781b224d5b8a 100644
--- a/lib/rubygems/commands/uninstall_command.rb
+++ b/lib/rubygems/commands/uninstall_command.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/version_option'
-require 'rubygems/uninstaller'
+require_relative '../command'
+require_relative '../version_option'
+require_relative '../uninstaller'
 require 'fileutils'
 
 ##
diff --git a/lib/rubygems/commands/unpack_command.rb b/lib/rubygems/commands/unpack_command.rb
index 8d90d08eb42adc..3f1708375f98e8 100644
--- a/lib/rubygems/commands/unpack_command.rb
+++ b/lib/rubygems/commands/unpack_command.rb
@@ -1,9 +1,9 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/version_option'
-require 'rubygems/security_option'
-require 'rubygems/remote_fetcher'
-require 'rubygems/package'
+require_relative '../command'
+require_relative '../version_option'
+require_relative '../security_option'
+require_relative '../remote_fetcher'
+require_relative '../package'
 
 # forward-declare
 
diff --git a/lib/rubygems/commands/update_command.rb b/lib/rubygems/commands/update_command.rb
index 91d93e398ca55f..d104488c943dd9 100644
--- a/lib/rubygems/commands/update_command.rb
+++ b/lib/rubygems/commands/update_command.rb
@@ -1,13 +1,13 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/command_manager'
-require 'rubygems/dependency_installer'
-require 'rubygems/install_update_options'
-require 'rubygems/local_remote_options'
-require 'rubygems/spec_fetcher'
-require 'rubygems/version_option'
-require 'rubygems/install_message' # must come before rdoc for messaging
-require 'rubygems/rdoc'
+require_relative '../command'
+require_relative '../command_manager'
+require_relative '../dependency_installer'
+require_relative '../install_update_options'
+require_relative '../local_remote_options'
+require_relative '../spec_fetcher'
+require_relative '../version_option'
+require_relative '../install_message' # must come before rdoc for messaging
+require_relative '../rdoc'
 
 class Gem::Commands::UpdateCommand < Gem::Command
   include Gem::InstallUpdateOptions
diff --git a/lib/rubygems/commands/which_command.rb b/lib/rubygems/commands/which_command.rb
index d42ab183956d89..44e87a2b988c76 100644
--- a/lib/rubygems/commands/which_command.rb
+++ b/lib/rubygems/commands/which_command.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require 'rubygems/command'
+require_relative '../command'
 
 class Gem::Commands::WhichCommand < Gem::Command
   def initialize
diff --git a/lib/rubygems/commands/yank_command.rb b/lib/rubygems/commands/yank_command.rb
index a7930253d69f71..cad78aec5f5a3c 100644
--- a/lib/rubygems/commands/yank_command.rb
+++ b/lib/rubygems/commands/yank_command.rb
@@ -1,8 +1,8 @@
 # frozen_string_literal: true
-require 'rubygems/command'
-require 'rubygems/local_remote_options'
-require 'rubygems/version_option'
-require 'rubygems/gemcutter_utilities'
+require_relative '../command'
+require_relative '../local_remote_options'
+require_relative '../version_option'
+require_relative '../gemcutter_utilities'
 
 class Gem::Commands::YankCommand < Gem::Command
   include Gem::LocalRemoteOptions
diff --git a/lib/rubygems/config_file.rb b/lib/rubygems/config_file.rb
index 02bb2be1220de3..60c1d50ba99bc5 100644
--- a/lib/rubygems/config_file.rb
+++ b/lib/rubygems/config_file.rb
@@ -5,7 +5,7 @@
 # See LICENSE.txt for permissions.
 #++
 
-require 'rubygems/user_interaction'
+require_relative 'user_interaction'
 require 'rbconfig'
 
 ##
diff --git a/lib/rubygems/dependency_installer.rb b/lib/rubygems/dependency_installer.rb
index 400a5de5cffd25..913bba32eb71c6 100644
--- a/lib/rubygems/dependency_installer.rb
+++ b/lib/rubygems/dependency_installer.rb
@@ -1,12 +1,12 @@
 # frozen_string_literal: true
-require 'rubygems'
-require 'rubygems/dependency_list'
-require 'rubygems/package'
-require 'rubygems/installer'
-require 'rubygems/spec_fetcher'
-require 'rubygems/user_interaction'
-require 'rubygems/available_set'
-require 'rubygems/deprecate'
+require_relative '../rubygems'
+require_relative 'dependency_list'
+require_relative 'package'
+require_relative 'installer'
+require_relative 'spec_fetcher'
+require_relative 'user_interaction'
+require_relative 'available_set'
+require_relative 'deprecate'
 
 ##
 # Installs a gem along with all its dependencies from local and remote gems.
diff --git a/lib/rubygems/dependency_list.rb b/lib/rubygems/dependency_list.rb
index bcf436cd03a995..8f61869874d581 100644
--- a/lib/rubygems/dependency_list.rb
+++ b/lib/rubygems/dependency_list.rb
@@ -6,7 +6,7 @@
 #++
 
 require 'tsort'
-require 'rubygems/deprecate'
+require_relative 'deprecate'
 
 ##
 # Gem::DependencyList is used for installing and uninstalling gems in the
diff --git a/lib/rubygems/doctor.rb b/lib/rubygems/doctor.rb
index ef31aeddd073ef..41bcda9804a749 100644
--- a/lib/rubygems/doctor.rb
+++ b/lib/rubygems/doctor.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
-require 'rubygems'
-require 'rubygems/user_interaction'
+require_relative '../rubygems'
+require_relative 'user_interaction'
 
 ##
 # Cleans up after a partially-failed uninstall or for an invalid
diff --git a/lib/rubygems/exceptions.rb b/lib/rubygems/exceptions.rb
index 185efdb6ab58dc..f0debb646ff5d3 100644
--- a/lib/rubygems/exceptions.rb
+++ b/lib/rubygems/exceptions.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
 
-require 'rubygems/deprecate'
-require 'rubygems/unknown_command_spell_checker'
+require_relative 'deprecate'
+require_relative 'unknown_command_spell_checker'
 
 ##
 # Base exception class for RubyGems.  All exception raised by RubyGems are a
diff --git a/lib/rubygems/gem_runner.rb b/lib/rubygems/gem_runner.rb
index a36674503eeef2..55b5a7d067771c 100644
--- a/lib/rubygems/gem_runner.rb
+++ b/lib/rubygems/gem_runner.rb
@@ -5,9 +5,9 @@
 # See LICENSE.txt for permissions.
 #++
 
-require 'rubygems'
-require 'rubygems/command_manager'
-require 'rubygems/deprecate'
+require_relative '../rubygems'
+require_relative 'command_manager'
+require_relative 'deprecate'
 
 ##
 # Load additional plugins from $LOAD_PATH
diff --git a/lib/rubygems/gemcutter_utilities.rb b/lib/rubygems/gemcutter_utilities.rb
index f4658810416eca..0968e1a6f90bf0 100644
--- a/lib/rubygems/gemcutter_utilities.rb
+++ b/lib/rubygems/gemcutter_utilities.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
-require 'rubygems/remote_fetcher'
-require 'rubygems/text'
+require_relative 'remote_fetcher'
+require_relative 'text'
 
 ##
 # Utility methods for using the RubyGems API.
diff --git a/lib/rubygems/indexer.rb b/lib/rubygems/indexer.rb
index e595459c878125..6e8dade6407b4a 100644
--- a/lib/rubygems/indexer.rb
+++ b/lib/rubygems/indexer.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
-require 'rubygems'
-require 'rubygems/package'
+require_relative '../rubygems'
+require_relative 'package'
 require 'tmpdir'
 
 ##
diff --git a/lib/rubygems/install_default_message.rb b/lib/rubygems/install_default_message.rb
index f68fd2fd04305b..052ef528e175a0 100644
--- a/lib/rubygems/install_default_message.rb
+++ b/lib/rubygems/install_default_message.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
-require 'rubygems'
-require 'rubygems/user_interaction'
+require_relative '../rubygems'
+require_relative 'user_interaction'
 
 ##
 # A post-install hook that displays "Successfully installed
diff --git a/lib/rubygems/install_message.rb b/lib/rubygems/install_message.rb
index 3c13888a84a3f9..861ead3770c1e5 100644
--- a/lib/rubygems/install_message.rb
+++ b/lib/rubygems/install_message.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
-require 'rubygems'
-require 'rubygems/user_interaction'
+require_relative '../rubygems'
+require_relative 'user_interaction'
 
 ##
 # A default post-install hook that displays "Successfully installed
diff --git a/lib/rubygems/install_update_options.rb b/lib/rubygems/install_update_options.rb
index 54a3950b64e668..cafa63544f9193 100644
--- a/lib/rubygems/install_update_options.rb
+++ b/lib/rubygems/install_update_options.rb
@@ -5,8 +5,8 @@
 # See LICENSE.txt for permissions.
 #++
 
-require 'rubygems'
-require 'rubygems/security_option'
+require_relative '../rubygems'
+require_relative 'security_option'
 
 ##
 # Mixin methods for install and update options for Gem::Commands
diff --git a/lib/rubygems/installer.rb b/lib/rubygems/installer.rb
index 6ab1f517d723c4..cf5ed7b502472b 100644
--- a/lib/rubygems/installer.rb
+++ b/lib/rubygems/installer.rb
@@ -5,13 +5,13 @@
 # See LICENSE.txt for permissions.
 #++
 
-require 'rubygems/command'
-require 'rubygems/installer_uninstaller_utils'
-require 'rubygems/exceptions'
-require 'rubygems/deprecate'
-require 'rubygems/package'
-require 'rubygems/ext'
-require 'rubygems/user_interaction'
+require_relative 'command'
+require_relative 'installer_uninstaller_utils'
+require_relative 'exceptions'
+require_relative 'deprecate'
+require_relative 'package'
+require_relative 'ext'
+require_relative 'user_interaction'
 
 ##
 # The installer installs the files contained in the .gem into the Gem.home.
diff --git a/lib/rubygems/local_remote_options.rb b/lib/rubygems/local_remote_options.rb
index 2d0509eb0326ef..8acd98d2e42f3a 100644
--- a/lib/rubygems/local_remote_options.rb
+++ b/lib/rubygems/local_remote_options.rb
@@ -6,7 +6,7 @@
 #++
 
 require 'uri'
-require 'rubygems'
+require_relative '../rubygems'
 
 ##
 # Mixin methods for local and remote Gem::Command options.
diff --git a/lib/rubygems/mock_gem_ui.rb b/lib/rubygems/mock_gem_ui.rb
index ec244fb7c669ef..914ecb9a71ef0f 100644
--- a/lib/rubygems/mock_gem_ui.rb
+++ b/lib/rubygems/mock_gem_ui.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require 'rubygems/user_interaction'
+require_relative 'user_interaction'
 
 ##
 # This Gem::StreamUI subclass records input and output to StringIO for
diff --git a/lib/rubygems/package.rb b/lib/rubygems/package.rb
index a4ae3e9ea50ce8..c4b29e4176de87 100644
--- a/lib/rubygems/package.rb
+++ b/lib/rubygems/package.rb
@@ -41,9 +41,9 @@
 # #files are the files in the .gem tar file, not the Ruby files in the gem
 # #extract_files and #contents automatically call #verify
 
-require "rubygems"
-require 'rubygems/security'
-require 'rubygems/user_interaction'
+require_relative "../rubygems"
+require_relative 'security'
+require_relative 'user_interaction'
 
 class Gem::Package
   include Gem::UserInteraction
@@ -702,12 +702,12 @@ def verify_gz(entry) # :nodoc:
   end
 end
 
-require 'rubygems/package/digest_io'
-require 'rubygems/package/source'
-require 'rubygems/package/file_source'
-require 'rubygems/package/io_source'
-require 'rubygems/package/old'
-require 'rubygems/package/tar_header'
-require 'rubygems/package/tar_reader'
-require 'rubygems/package/tar_reader/entry'
-require 'rubygems/package/tar_writer'
+require_relative 'package/digest_io'
+require_relative 'package/source'
+require_relative 'package/file_source'
+require_relative 'package/io_source'
+require_relative 'package/old'
+require_relative 'package/tar_header'
+require_relative 'package/tar_reader'
+require_relative 'package/tar_reader/entry'
+require_relative 'package/tar_writer'
diff --git a/lib/rubygems/package/tar_reader.rb b/lib/rubygems/package/tar_reader.rb
index e7c5620533e3f7..41121f3bfb39b8 100644
--- a/lib/rubygems/package/tar_reader.rb
+++ b/lib/rubygems/package/tar_reader.rb
@@ -121,4 +121,4 @@ def seek(name) # :yields: entry
   end
 end
 
-require 'rubygems/package/tar_reader/entry'
+require_relative 'tar_reader/entry'
diff --git a/lib/rubygems/package_task.rb b/lib/rubygems/package_task.rb
index d5a2885a64ec3f..bb48616b0eeccf 100644
--- a/lib/rubygems/package_task.rb
+++ b/lib/rubygems/package_task.rb
@@ -20,8 +20,8 @@
 # OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION
 # WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.
 
-require 'rubygems'
-require 'rubygems/package'
+require_relative '../rubygems'
+require_relative 'package'
 require 'rake/packagetask'
 
 ##
diff --git a/lib/rubygems/platform.rb b/lib/rubygems/platform.rb
index fd1c0a62ac7a96..9750df181bceb6 100644
--- a/lib/rubygems/platform.rb
+++ b/lib/rubygems/platform.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require "rubygems/deprecate"
+require_relative "deprecate"
 
 ##
 # Available list of platforms for targeting Gem installations.
diff --git a/lib/rubygems/rdoc.rb b/lib/rubygems/rdoc.rb
index c40bb7d9f17ac3..ac5e8f082200dc 100644
--- a/lib/rubygems/rdoc.rb
+++ b/lib/rubygems/rdoc.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require 'rubygems'
+require_relative '../rubygems'
 
 begin
   require 'rdoc/rubygems_hook'
diff --git a/lib/rubygems/remote_fetcher.rb b/lib/rubygems/remote_fetcher.rb
index 45dca1195e9feb..8c9c9e6150fc68 100644
--- a/lib/rubygems/remote_fetcher.rb
+++ b/lib/rubygems/remote_fetcher.rb
@@ -1,11 +1,11 @@
 # frozen_string_literal: true
-require 'rubygems'
-require 'rubygems/request'
-require 'rubygems/request/connection_pools'
-require 'rubygems/s3_uri_signer'
-require 'rubygems/uri_formatter'
-require 'rubygems/uri_parser'
-require 'rubygems/user_interaction'
+require_relative '../rubygems'
+require_relative 'request'
+require_relative 'request/connection_pools'
+require_relative 's3_uri_signer'
+require_relative 'uri_formatter'
+require_relative 'uri_parser'
+require_relative 'user_interaction'
 
 ##
 # RemoteFetcher handles the details of fetching gems and gem information from
diff --git a/lib/rubygems/request.rb b/lib/rubygems/request.rb
index 5bda0b2e5e92bd..16a368e5ae8272 100644
--- a/lib/rubygems/request.rb
+++ b/lib/rubygems/request.rb
@@ -1,6 +1,6 @@
 # frozen_string_literal: true
 require 'net/http'
-require 'rubygems/user_interaction'
+require_relative 'user_interaction'
 
 class Gem::Request
   extend Gem::UserInteraction
@@ -287,6 +287,6 @@ def user_agent
   end
 end
 
-require 'rubygems/request/http_pool'
-require 'rubygems/request/https_pool'
-require 'rubygems/request/connection_pools'
+require_relative 'request/http_pool'
+require_relative 'request/https_pool'
+require_relative 'request/connection_pools'
diff --git a/lib/rubygems/request_set.rb b/lib/rubygems/request_set.rb
index 36ec87e1f7447d..9286c542219b2f 100644
--- a/lib/rubygems/request_set.rb
+++ b/lib/rubygems/request_set.rb
@@ -303,7 +303,7 @@ def install_hooks(requests, options)
       end
     end
 
-    require "rubygems/dependency_installer"
+    require_relative "dependency_installer"
     inst = Gem::DependencyInstaller.new options
     inst.installed_gems.replace specs
 
@@ -461,6 +461,6 @@ def tsort_each_child(node) # :nodoc:
   end
 end
 
-require 'rubygems/request_set/gem_dependency_api'
-require 'rubygems/request_set/lockfile'
-require 'rubygems/request_set/lockfile/tokenizer'
+require_relative 'request_set/gem_dependency_api'
+require_relative 'request_set/lockfile'
+require_relative 'request_set/lockfile/tokenizer'
diff --git a/lib/rubygems/request_set/lockfile.rb b/lib/rubygems/request_set/lockfile.rb
index 8f8f142fffe05b..bec29ef1b97a14 100644
--- a/lib/rubygems/request_set/lockfile.rb
+++ b/lib/rubygems/request_set/lockfile.rb
@@ -236,4 +236,4 @@ def requests
   end
 end
 
-require 'rubygems/request_set/lockfile/tokenizer'
+require_relative 'lockfile/tokenizer'
diff --git a/lib/rubygems/request_set/lockfile/tokenizer.rb b/lib/rubygems/request_set/lockfile/tokenizer.rb
index 6918e8e1a5b3dd..cb8030c143d71f 100644
--- a/lib/rubygems/request_set/lockfile/tokenizer.rb
+++ b/lib/rubygems/request_set/lockfile/tokenizer.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require 'rubygems/request_set/lockfile/parser'
+require_relative 'parser'
 
 class Gem::RequestSet::Lockfile::Tokenizer
   Token = Struct.new :type, :value, :column, :line
diff --git a/lib/rubygems/requirement.rb b/lib/rubygems/requirement.rb
index 16de45ad919c1e..d2e28fab5b4944 100644
--- a/lib/rubygems/requirement.rb
+++ b/lib/rubygems/requirement.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require "rubygems/deprecate"
+require_relative "deprecate"
 
 ##
 # A Requirement is a set of one or more version restrictions. It supports a
diff --git a/lib/rubygems/resolver.rb b/lib/rubygems/resolver.rb
index 71c35ea3d37c84..51a11fed474745 100644
--- a/lib/rubygems/resolver.rb
+++ b/lib/rubygems/resolver.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
-require 'rubygems/dependency'
-require 'rubygems/exceptions'
-require 'rubygems/util/list'
+require_relative 'dependency'
+require_relative 'exceptions'
+require_relative 'util/list'
 
 ##
 # Given a set of Gem::Dependency objects as +needed+ and a way to query the
@@ -10,7 +10,7 @@
 # all the requirements.
 
 class Gem::Resolver
-  require 'rubygems/resolver/molinillo'
+  require_relative 'resolver/molinillo'
 
   ##
   # If the DEBUG_RESOLVER environment variable is set then debugging mode is
@@ -318,30 +318,30 @@ def amount_constrained(dependency)
   private :amount_constrained
 end
 
-require 'rubygems/resolver/activation_request'
-require 'rubygems/resolver/conflict'
-require 'rubygems/resolver/dependency_request'
-require 'rubygems/resolver/requirement_list'
-require 'rubygems/resolver/stats'
-
-require 'rubygems/resolver/set'
-require 'rubygems/resolver/api_set'
-require 'rubygems/resolver/composed_set'
-require 'rubygems/resolver/best_set'
-require 'rubygems/resolver/current_set'
-require 'rubygems/resolver/git_set'
-require 'rubygems/resolver/index_set'
-require 'rubygems/resolver/installer_set'
-require 'rubygems/resolver/lock_set'
-require 'rubygems/resolver/vendor_set'
-require 'rubygems/resolver/source_set'
-
-require 'rubygems/resolver/specification'
-require 'rubygems/resolver/spec_specification'
-require 'rubygems/resolver/api_specification'
-require 'rubygems/resolver/git_specification'
-require 'rubygems/resolver/index_specification'
-require 'rubygems/resolver/installed_specification'
-require 'rubygems/resolver/local_specification'
-require 'rubygems/resolver/lock_specification'
-require 'rubygems/resolver/vendor_specification'
+require_relative 'resolver/activation_request'
+require_relative 'resolver/conflict'
+require_relative 'resolver/dependency_request'
+require_relative 'resolver/requirement_list'
+require_relative 'resolver/stats'
+
+require_relative 'resolver/set'
+require_relative 'resolver/api_set'
+require_relative 'resolver/composed_set'
+require_relative 'resolver/best_set'
+require_relative 'resolver/current_set'
+require_relative 'resolver/git_set'
+require_relative 'resolver/index_set'
+require_relative 'resolver/installer_set'
+require_relative 'resolver/lock_set'
+require_relative 'resolver/vendor_set'
+require_relative 'resolver/source_set'
+
+require_relative 'resolver/specification'
+require_relative 'resolver/spec_specification'
+require_relative 'resolver/api_specification'
+require_relative 'resolver/git_specification'
+require_relative 'resolver/index_specification'
+require_relative 'resolver/installed_specification'
+require_relative 'resolver/local_specification'
+require_relative 'resolver/lock_specification'
+require_relative 'resolver/vendor_specification'
diff --git a/lib/rubygems/resolver/git_specification.rb b/lib/rubygems/resolver/git_specification.rb
index 555dcffc22eff8..ee47080ab46594 100644
--- a/lib/rubygems/resolver/git_specification.rb
+++ b/lib/rubygems/resolver/git_specification.rb
@@ -21,7 +21,7 @@ def add_dependency(dependency) # :nodoc:
   # the executables.
 
   def install(options = {})
-    require 'rubygems/installer'
+    require_relative '../installer'
 
     installer = Gem::Installer.for_spec spec, options
 
diff --git a/lib/rubygems/resolver/molinillo.rb b/lib/rubygems/resolver/molinillo.rb
index 2357f41bee1e25..12ca740e5acb39 100644
--- a/lib/rubygems/resolver/molinillo.rb
+++ b/lib/rubygems/resolver/molinillo.rb
@@ -1,2 +1,2 @@
 # frozen_string_literal: true
-require 'rubygems/resolver/molinillo/lib/molinillo'
+require_relative 'molinillo/lib/molinillo'
diff --git a/lib/rubygems/resolver/specification.rb b/lib/rubygems/resolver/specification.rb
index 8c6fc9afcf92cb..dfcb7eb05721d7 100644
--- a/lib/rubygems/resolver/specification.rb
+++ b/lib/rubygems/resolver/specification.rb
@@ -93,7 +93,7 @@ def full_name
   # specification.
 
   def install(options = {})
-    require 'rubygems/installer'
+    require_relative '../installer'
 
     gem = download options
 
diff --git a/lib/rubygems/security.rb b/lib/rubygems/security.rb
index c80639af6d0ed9..28f705549c83e6 100644
--- a/lib/rubygems/security.rb
+++ b/lib/rubygems/security.rb
@@ -5,7 +5,7 @@
 # See LICENSE.txt for permissions.
 #++
 
-require 'rubygems/exceptions'
+require_relative 'exceptions'
 require_relative 'openssl'
 
 ##
@@ -592,9 +592,9 @@ def self.write(pemmable, path, permissions = 0600, passphrase = nil, cipher = KE
 end
 
 if Gem::HAVE_OPENSSL
-  require 'rubygems/security/policy'
-  require 'rubygems/security/policies'
-  require 'rubygems/security/trust_dir'
+  require_relative 'security/policy'
+  require_relative 'security/policies'
+  require_relative 'security/trust_dir'
 end
 
-require 'rubygems/security/signer'
+require_relative 'security/signer'
diff --git a/lib/rubygems/security/policy.rb b/lib/rubygems/security/policy.rb
index 7629d64796c735..9683e55b327e30 100644
--- a/lib/rubygems/security/policy.rb
+++ b/lib/rubygems/security/policy.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require 'rubygems/user_interaction'
+require_relative '../user_interaction'
 
 ##
 # A Gem::Security::Policy object encapsulates the settings for verifying
diff --git a/lib/rubygems/security/signer.rb b/lib/rubygems/security/signer.rb
index 6c85ab08d29506..c5c2c4f22004c7 100644
--- a/lib/rubygems/security/signer.rb
+++ b/lib/rubygems/security/signer.rb
@@ -2,7 +2,7 @@
 ##
 # Basic OpenSSL-based package signing class.
 
-require "rubygems/user_interaction"
+require_relative "../user_interaction"
 
 class Gem::Security::Signer
   include Gem::UserInteraction
diff --git a/lib/rubygems/security_option.rb b/lib/rubygems/security_option.rb
index 3403aaaf05f827..6c75d6ecb4f0ba 100644
--- a/lib/rubygems/security_option.rb
+++ b/lib/rubygems/security_option.rb
@@ -5,7 +5,7 @@
 # See LICENSE.txt for permissions.
 #++
 
-require 'rubygems'
+require_relative '../rubygems'
 
 # forward-declare
 
@@ -20,7 +20,7 @@ class Policy # :nodoc:
 module Gem::SecurityOption
   def add_security_option
     OptionParser.accept Gem::Security::Policy do |value|
-      require 'rubygems/security'
+      require_relative 'security'
 
       raise OptionParser::InvalidArgument, 'OpenSSL not installed' unless
         defined?(Gem::Security::HighSecurity)
diff --git a/lib/rubygems/server.rb b/lib/rubygems/server.rb
index 2c2805f31ce383..45be05bcda7ec0 100644
--- a/lib/rubygems/server.rb
+++ b/lib/rubygems/server.rb
@@ -3,8 +3,8 @@
 require 'erb'
 require 'uri'
 
-require 'rubygems'
-require 'rubygems/rdoc'
+require_relative '../rubygems'
+require_relative 'rdoc'
 
 ##
 # Gem::Server and allows users to serve gems for consumption by
diff --git a/lib/rubygems/source.rb b/lib/rubygems/source.rb
index 37e03cdfaea5c8..a9d91ed18eeef9 100644
--- a/lib/rubygems/source.rb
+++ b/lib/rubygems/source.rb
@@ -240,9 +240,9 @@ def enforce_trailing_slash(uri)
   end
 end
 
-require 'rubygems/source/git'
-require 'rubygems/source/installed'
-require 'rubygems/source/specific_file'
-require 'rubygems/source/local'
-require 'rubygems/source/lock'
-require 'rubygems/source/vendor'
+require_relative 'source/git'
+require_relative 'source/installed'
+require_relative 'source/specific_file'
+require_relative 'source/local'
+require_relative 'source/lock'
+require_relative 'source/vendor'
diff --git a/lib/rubygems/spec_fetcher.rb b/lib/rubygems/spec_fetcher.rb
index b2bcadc49cd941..68ff605a832b25 100644
--- a/lib/rubygems/spec_fetcher.rb
+++ b/lib/rubygems/spec_fetcher.rb
@@ -1,9 +1,9 @@
 # frozen_string_literal: true
-require 'rubygems/remote_fetcher'
-require 'rubygems/user_interaction'
-require 'rubygems/errors'
-require 'rubygems/text'
-require 'rubygems/name_tuple'
+require_relative 'remote_fetcher'
+require_relative 'user_interaction'
+require_relative 'errors'
+require_relative 'text'
+require_relative 'name_tuple'
 
 ##
 # SpecFetcher handles metadata updates from remote gem repositories.
diff --git a/lib/rubygems/specification.rb b/lib/rubygems/specification.rb
index ff345bf7a368d1..83277fd281df6e 100644
--- a/lib/rubygems/specification.rb
+++ b/lib/rubygems/specification.rb
@@ -6,11 +6,11 @@
 # See LICENSE.txt for permissions.
 #++
 
-require 'rubygems/deprecate'
-require 'rubygems/basic_specification'
-require 'rubygems/stub_specification'
-require 'rubygems/specification_policy'
-require 'rubygems/util/list'
+require_relative 'deprecate'
+require_relative 'basic_specification'
+require_relative 'stub_specification'
+require_relative 'specification_policy'
+require_relative 'util/list'
 
 ##
 # The Specification class contains the information for a gem.  Typically
@@ -1568,9 +1568,9 @@ def build_extensions # :nodoc:
       unresolved_deps = Gem::Specification.unresolved_deps.dup
       Gem::Specification.unresolved_deps.clear
 
-      require 'rubygems/config_file'
-      require 'rubygems/ext'
-      require 'rubygems/user_interaction'
+      require_relative 'config_file'
+      require_relative 'ext'
+      require_relative 'user_interaction'
 
       ui = Gem::SilentUI.new
       Gem::DefaultUserInteraction.use_ui ui do
@@ -2525,7 +2525,7 @@ def to_yaml(opts = {}) # :nodoc:
     # back, we have to check again here to make sure that our
     # psych code was properly loaded, and load it if not.
     unless Gem.const_defined?(:NoAliasYAMLTree)
-      require 'rubygems/psych_tree'
+      require_relative 'psych_tree'
     end
 
     builder = Gem::NoAliasYAMLTree.create
diff --git a/lib/rubygems/specification_policy.rb b/lib/rubygems/specification_policy.rb
index 86277a20584ea6..1f1f73b11f8875 100644
--- a/lib/rubygems/specification_policy.rb
+++ b/lib/rubygems/specification_policy.rb
@@ -1,4 +1,4 @@
-require 'rubygems/user_interaction'
+require_relative 'user_interaction'
 
 class Gem::SpecificationPolicy
   include Gem::UserInteraction
diff --git a/lib/rubygems/uninstaller.rb b/lib/rubygems/uninstaller.rb
index 87a5ef770f3329..11fb6113291305 100644
--- a/lib/rubygems/uninstaller.rb
+++ b/lib/rubygems/uninstaller.rb
@@ -6,11 +6,11 @@
 #++
 
 require 'fileutils'
-require 'rubygems'
-require 'rubygems/installer_uninstaller_utils'
-require 'rubygems/dependency_list'
-require 'rubygems/rdoc'
-require 'rubygems/user_interaction'
+require_relative '../rubygems'
+require_relative 'installer_uninstaller_utils'
+require_relative 'dependency_list'
+require_relative 'rdoc'
+require_relative 'user_interaction'
 
 ##
 # An Uninstaller.
@@ -360,7 +360,7 @@ def formatted_program_filename(filename) # :nodoc:
     # of what it did for us to find rather than trying to recreate
     # it again.
     if @format_executable
-      require 'rubygems/installer'
+      require_relative 'installer'
       Gem::Installer.exec_format % File.basename(filename)
     else
       filename
diff --git a/lib/rubygems/user_interaction.rb b/lib/rubygems/user_interaction.rb
index 6376ea7cf8e74d..0ab44fbf6cc85b 100644
--- a/lib/rubygems/user_interaction.rb
+++ b/lib/rubygems/user_interaction.rb
@@ -5,8 +5,8 @@
 # See LICENSE.txt for permissions.
 #++
 
-require 'rubygems/deprecate'
-require 'rubygems/text'
+require_relative 'deprecate'
+require_relative 'text'
 
 ##
 # Module that defines the default UserInteraction.  Any class including this
diff --git a/lib/rubygems/util/licenses.rb b/lib/rubygems/util/licenses.rb
index 98cbd8929bc735..8de5b11ae38fec 100644
--- a/lib/rubygems/util/licenses.rb
+++ b/lib/rubygems/util/licenses.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
-require 'rubygems/text'
+require_relative '../text'
 
 class Gem::Licenses
   extend Gem::Text
diff --git a/lib/rubygems/validator.rb b/lib/rubygems/validator.rb
index 30cdd93b5ca583..728595e7785c21 100644
--- a/lib/rubygems/validator.rb
+++ b/lib/rubygems/validator.rb
@@ -5,8 +5,8 @@
 # See LICENSE.txt for permissions.
 #++
 
-require 'rubygems/package'
-require 'rubygems/installer'
+require_relative 'package'
+require_relative 'installer'
 
 ##
 # Validator performs various gem file and gem database validation
diff --git a/lib/rubygems/version_option.rb b/lib/rubygems/version_option.rb
index be71ef409b4b7d..eabe4fdb5760b6 100644
--- a/lib/rubygems/version_option.rb
+++ b/lib/rubygems/version_option.rb
@@ -5,7 +5,7 @@
 # See LICENSE.txt for permissions.
 #++
 
-require 'rubygems'
+require_relative '../rubygems'
 
 ##
 # Mixin methods for --version and --platform Gem::Command options.