diff --git a/lib/rubygems.rb b/lib/rubygems.rb
index 21af9ac8f841..a18cb9905bcb 100644
--- a/lib/rubygems.rb
+++ b/lib/rubygems.rb
@@ -266,17 +266,10 @@ def self.find_spec_for_exe(name, exec_name, requirements)
 
     return loaded if loaded && dep.matches_spec?(loaded)
 
-    specs = dep.matching_specs(true)
+    spec = dep.spec_for_exe(exec_name)
 
-    specs = specs.find_all do |spec|
-      spec.executables.include? exec_name
-    end if exec_name
-
-    unless spec = specs.first
+    unless spec
       msg = "can't find gem #{dep} with executable #{exec_name}"
-      if name == "bundler" && bundler_message = Gem::BundlerVersionFinder.missing_version_message
-        msg = bundler_message
-      end
       raise Gem::GemNotFoundException, msg
     end
 
@@ -1182,6 +1175,8 @@ def self.use_gemdeps(path = nil)
     end
 
     ENV["BUNDLE_GEMFILE"] ||= File.expand_path(path)
+    ENV["BUNDLE_PATH__SYSTEM"] ||= "true"
+
     require 'rubygems/user_interaction'
     Gem::DefaultUserInteraction.use_ui(ui) do
       require "bundler"
diff --git a/lib/rubygems/bundler_version_finder.rb b/lib/rubygems/bundler_version_finder.rb
index e74baca1ee67..8d03dce0f9c9 100644
--- a/lib/rubygems/bundler_version_finder.rb
+++ b/lib/rubygems/bundler_version_finder.rb
@@ -41,10 +41,11 @@ def self.compatible?(spec)
     spec.version.segments.first == bundler_version.segments.first
   end
 
-  def self.filter!(specs)
-    return unless bundler_version = self.bundler_version
+  def self.prioritize!(specs)
+    match_index = specs.find_index { |spec| compatible?(spec) }
+    return unless match_index
 
-    specs.reject! { |spec| spec.version.segments.first != bundler_version.segments.first }
+    specs.unshift(specs.delete_at(match_index))
   end
 
   def self.bundle_update_bundler_version
diff --git a/lib/rubygems/core_ext/kernel_require.rb b/lib/rubygems/core_ext/kernel_require.rb
index 3b7801161978..014090a16ef7 100755
--- a/lib/rubygems/core_ext/kernel_require.rb
+++ b/lib/rubygems/core_ext/kernel_require.rb
@@ -39,7 +39,7 @@ def require(path)
     if spec = Gem.find_unresolved_default_spec(path)
       Gem.remove_unresolved_default_spec(spec)
       begin
-        Kernel.send(:gem, spec.name)
+        Kernel.send(:gem, spec.name, "#{Gem::Requirement.default}.a")
       rescue Exception
         RUBYGEMS_ACTIVATION_MONITOR.exit
         raise
diff --git a/lib/rubygems/dependency.rb b/lib/rubygems/dependency.rb
index 3c91392cdd6b..8c35ab49c762 100644
--- a/lib/rubygems/dependency.rb
+++ b/lib/rubygems/dependency.rb
@@ -281,7 +281,7 @@ def matching_specs(platform_only = false)
       requirement.satisfied_by?(spec.version) && env_req.satisfied_by?(spec.version)
     end.map(&:to_spec)
 
-    Gem::BundlerVersionFinder.filter!(matches) if name == "bundler".freeze
+    Gem::BundlerVersionFinder.prioritize!(matches) if name == "bundler".freeze
 
     if platform_only
       matches.reject! do |spec|
@@ -325,13 +325,36 @@ def to_spec
     active = matches.find { |spec| spec.activated? }
     return active if active
 
-    return matches.first if prerelease?
+    unless prerelease?
+      # Move prereleases to the end of the list for >= 0 requirements
+      pre, matches = matches.partition { |spec| spec.version.prerelease? }
+      matches += pre if requirement == Gem::Requirement.default
+    end
+
+    select_first(matches)
+  end
+
+  def spec_for_exe(exec_name)
+    matches = matching_specs(true)
+
+    matches = matches.find_all do |spec|
+      spec.executables.include? exec_name
+    end if exec_name
 
-    # Move prereleases to the end of the list for >= 0 requirements
-    pre, matches = matches.partition { |spec| spec.version.prerelease? }
-    matches += pre if requirement == Gem::Requirement.default
+    select_first(matches)
+  end
+
+  private
+
+  def select_first(matches)
+    spec = matches.first
+    return unless spec
+
+    if !Gem::BundlerVersionFinder.compatible?(spec)
+      warn Gem::BundlerVersionFinder.missing_version_message
+    end
 
-    matches.first
+    spec
   end
 
 end
diff --git a/lib/rubygems/errors.rb b/lib/rubygems/errors.rb
index 2cd18e2e20f0..446cfc6cee51 100644
--- a/lib/rubygems/errors.rb
+++ b/lib/rubygems/errors.rb
@@ -63,9 +63,6 @@ def initialize(name, requirement, specs)
     private
 
     def build_message
-      if name == "bundler" && message = Gem::BundlerVersionFinder.missing_version_message
-        return message
-      end
       names = specs.map(&:full_name)
       "Could not find '#{name}' (#{requirement}) - did find: [#{names.join ','}]\n"
     end
diff --git a/test/rubygems/test_gem.rb b/test/rubygems/test_gem.rb
index af927ffa29be..1d6484502006 100644
--- a/test/rubygems/test_gem.rb
+++ b/test/rubygems/test_gem.rb
@@ -329,14 +329,14 @@ def test_activate_bin_path_gives_proper_error_for_bundler
 
     File.open("Gemfile", "w") { |f| f.puts('source "https://rubygems.org"') }
 
-    e = assert_raises Gem::GemNotFoundException do
+    _, err = capture_io do
       load Gem.activate_bin_path("bundler", "bundle", ">= 0.a")
     end
 
-    assert_includes e.message, "Could not find 'bundler' (9999) required by your #{File.expand_path("Gemfile.lock")}."
-    assert_includes e.message, "To update to the latest version installed on your system, run `bundle update --bundler`."
-    assert_includes e.message, "To install the missing version, run `gem install bundler:9999`"
-    refute_includes e.message, "can't find gem bundler (>= 0.a) with executable bundle"
+    assert_includes err, "Could not find 'bundler' (9999) required by your #{File.expand_path("Gemfile.lock")}."
+    assert_includes err, "To update to the latest version installed on your system, run `bundle update --bundler`."
+    assert_includes err, "To install the missing version, run `gem install bundler:9999`"
+    refute_includes err, "can't find gem bundler (>= 0.a) with executable bundle"
   end
 
   def test_self_bin_path_no_exec_name
@@ -1824,11 +1824,21 @@ def test_use_gemdeps_missing_gem
       platform = " #{platform}"
     end
 
-    expected = <<-EXPECTED
+    expected =
+      if Bundler.feature_flag.lockfile_uses_separate_rubygems_sources?
+        <<-EXPECTED
+Could not find gem 'a' in locally installed gems.
+The source does not contain any versions of 'a'
+You may need to `gem install -g` to install missing gems
+
+        EXPECTED
+      else
+        <<-EXPECTED
 Could not find gem 'a#{platform}' in any of the gem sources listed in your Gemfile.
 You may need to `gem install -g` to install missing gems
 
-    EXPECTED
+        EXPECTED
+      end
 
     assert_output nil, expected do
       Gem.use_gemdeps
diff --git a/test/rubygems/test_gem_bundler_version_finder.rb b/test/rubygems/test_gem_bundler_version_finder.rb
index 8e883bc71984..235afbcc1ad7 100644
--- a/test/rubygems/test_gem_bundler_version_finder.rb
+++ b/test/rubygems/test_gem_bundler_version_finder.rb
@@ -100,33 +100,33 @@ def test_compatible
     end
   end
 
-  def test_filter
+  def test_prioritize
     versions = %w[1 1.0 1.0.1.1 2 2.a 2.0 2.1.1 3 3.a 3.0 3.1.1]
     specs = versions.map { |v| util_spec("bundler", v) }
 
-    assert_equal %w[1 1.0 1.0.1.1 2 2.a 2.0 2.1.1 3 3.a 3.0 3.1.1], util_filter_specs(specs).map(&:version).map(&:to_s)
+    assert_equal %w[1 1.0 1.0.1.1 2 2.a 2.0 2.1.1 3 3.a 3.0 3.1.1], util_prioritize_specs(specs)
 
     bvf.stub(:bundler_version, v("2.1.1.1")) do
-      assert_equal %w[2 2.a 2.0 2.1.1], util_filter_specs(specs).map(&:version).map(&:to_s)
+      assert_equal %w[2 1 1.0 1.0.1.1 2.a 2.0 2.1.1 3 3.a 3.0 3.1.1], util_prioritize_specs(specs)
     end
     bvf.stub(:bundler_version, v("1.1.1.1")) do
-      assert_equal %w[1 1.0 1.0.1.1], util_filter_specs(specs).map(&:version).map(&:to_s)
+      assert_equal %w[1 1.0 1.0.1.1 2 2.a 2.0 2.1.1 3 3.a 3.0 3.1.1], util_prioritize_specs(specs)
     end
     bvf.stub(:bundler_version, v("1")) do
-      assert_equal %w[1 1.0 1.0.1.1], util_filter_specs(specs).map(&:version).map(&:to_s)
+      assert_equal %w[1 1.0 1.0.1.1 2 2.a 2.0 2.1.1 3 3.a 3.0 3.1.1], util_prioritize_specs(specs)
     end
     bvf.stub(:bundler_version, v("2.a")) do
-      assert_equal %w[2 2.a 2.0 2.1.1], util_filter_specs(specs).map(&:version).map(&:to_s)
+      assert_equal %w[2 1 1.0 1.0.1.1 2.a 2.0 2.1.1 3 3.a 3.0 3.1.1], util_prioritize_specs(specs)
     end
     bvf.stub(:bundler_version, v("3")) do
-      assert_equal %w[3 3.a 3.0 3.1.1], util_filter_specs(specs).map(&:version).map(&:to_s)
+      assert_equal %w[3 1 1.0 1.0.1.1 2 2.a 2.0 2.1.1 3.a 3.0 3.1.1], util_prioritize_specs(specs)
     end
   end
 
-  def util_filter_specs(specs)
+  def util_prioritize_specs(specs)
     specs = specs.dup
-    bvf.filter!(specs)
-    specs
+    bvf.prioritize!(specs)
+    specs.map(&:version).map(&:to_s)
   end
 
 end
diff --git a/test/rubygems/test_gem_dependency.rb b/test/rubygems/test_gem_dependency.rb
index bf2f0655732e..e96711322601 100644
--- a/test/rubygems/test_gem_dependency.rb
+++ b/test/rubygems/test_gem_dependency.rb
@@ -353,16 +353,12 @@ def test_to_specs_respects_bundler_version
 
     assert_equal [b, b_1], dep.to_specs
 
-    Gem::BundlerVersionFinder.stub(:bundler_version_with_reason, ["3.5", "reason"]) do
-      e = assert_raises Gem::MissingSpecVersionError do
-        dep.to_specs
-      end
-
-      assert_match "Could not find 'bundler' (3.5) required by reason.\nTo update to the latest version installed on your system, run `bundle update --bundler`.\nTo install the missing version, run `gem install bundler:3.5`\n", e.message
+    Gem::BundlerVersionFinder.stub(:bundler_version_with_reason, ["1.16", "reason"]) do
+      assert_equal [b_1, b], dep.to_specs
     end
 
     Gem::BundlerVersionFinder.stub(:bundler_version_with_reason, ["2.0.0.pre.1", "reason"]) do
-      assert_equal [b], dep.to_specs
+      assert_equal [b, b_1], dep.to_specs
     end
   end
 
diff --git a/test/rubygems/test_kernel.rb b/test/rubygems/test_kernel.rb
index b9f9b5e2544d..d562820919d7 100644
--- a/test/rubygems/test_kernel.rb
+++ b/test/rubygems/test_kernel.rb
@@ -104,10 +104,10 @@ def test_gem_bundler_missing_bundler_version
       quick_gem 'bundler', '1'
       quick_gem 'bundler', '2.a'
 
-      e = assert_raises Gem::MissingSpecVersionError do
+      _, e = capture_io do
         gem('bundler')
       end
-      assert_match "Could not find 'bundler' (55) required by reason.", e.message
+      assert_match "Could not find 'bundler' (55) required by reason.", e
     end
   end
 
diff --git a/test/rubygems/test_require.rb b/test/rubygems/test_require.rb
index 16159ef65e90..2e3664a3384f 100644
--- a/test/rubygems/test_require.rb
+++ b/test/rubygems/test_require.rb
@@ -323,6 +323,19 @@ def test_default_gem_and_normal_gem
     assert_equal %w(default-3.0), loaded_spec_names
   end
 
+  def test_default_gem_prerelease
+    default_gem_spec = new_default_spec("default", "2.0.0",
+                                        nil, "default/gem.rb")
+    install_default_specs(default_gem_spec)
+
+    default_gem_prerelease_spec = new_default_spec("default", "3.0.0.rc2",
+                                                  nil, "default/gem.rb")
+    install_default_specs(default_gem_prerelease_spec)
+
+    assert_require "default/gem"
+    assert_equal %w(default-3.0.0.rc2), loaded_spec_names
+  end
+
   def loaded_spec_names
     Gem.loaded_specs.values.map(&:full_name).sort
   end
@@ -399,10 +412,10 @@ def test_require_bundler_missing_bundler_version
       b2a = util_spec('bundler', '2.a', nil, "lib/bundler/setup.rb")
       install_specs b1, b2a
 
-      e = assert_raises Gem::MissingSpecVersionError do
+      _, e = capture_io do
         gem('bundler')
       end
-      assert_match "Could not find 'bundler' (55) required by reason.", e.message
+      assert_match "Could not find 'bundler' (55) required by reason.", e
     end
   end