diff --git a/lib/rubygems/basic_specification.rb b/lib/rubygems/basic_specification.rb
index 0d50a93230..72954a7863 100644
--- a/lib/rubygems/basic_specification.rb
+++ b/lib/rubygems/basic_specification.rb
@@ -275,10 +275,14 @@ class Gem::BasicSpecification
   # for this spec.
 
   def lib_dirs_glob
-    dirs = if self.raw_require_paths.size > 1 then
-             "{#{self.raw_require_paths.join(',')}}"
+    dirs = if self.raw_require_paths
+             if self.raw_require_paths.size > 1 then
+               "{#{self.raw_require_paths.join(',')}}"
+             else
+               self.raw_require_paths.first
+             end
            else
-             self.raw_require_paths.first
+            "lib" # default value for require_paths for bundler/inline
            end
 
     "#{self.full_gem_path}/#{dirs}".dup.untaint
diff --git a/test/rubygems/test_gem_stream_ui.rb b/test/rubygems/test_gem_stream_ui.rb
index 9518ebc88e..51fd51c474 100644
--- a/test/rubygems/test_gem_stream_ui.rb
+++ b/test/rubygems/test_gem_stream_ui.rb
@@ -37,7 +37,7 @@ class TestGemStreamUI < Gem::TestCase
 
   def test_ask
     skip 'TTY detection broken on windows' if
-      Gem.win_platform? unless RUBY_VERSION > '1.9.2'
+      Gem.win_platform? && RUBY_VERSION <= '1.9.2'
 
     Timeout.timeout(1) do
       expected_answer = "Arthur, King of the Britons"
@@ -49,7 +49,7 @@ class TestGemStreamUI < Gem::TestCase
 
   def test_ask_no_tty
     skip 'TTY detection broken on windows' if
-      Gem.win_platform? unless RUBY_VERSION > '1.9.2'
+      Gem.win_platform? && RUBY_VERSION <= '1.9.2'
 
     @in.tty = false
 
@@ -61,7 +61,7 @@ class TestGemStreamUI < Gem::TestCase
 
   def test_ask_for_password
     skip 'Always uses $stdin on windows' if
-      Gem.win_platform? unless RUBY_VERSION > '1.9.2'
+      Gem.win_platform? && RUBY_VERSION <= '1.9.2'
 
     Timeout.timeout(1) do
       expected_answer = "Arthur, King of the Britons"
@@ -73,7 +73,7 @@ class TestGemStreamUI < Gem::TestCase
 
   def test_ask_for_password_no_tty
     skip 'TTY handling is broken on windows' if
-      Gem.win_platform? unless RUBY_VERSION > '1.9.2'
+      Gem.win_platform? && RUBY_VERSION <= '1.9.2'
 
     @in.tty = false
 
@@ -85,7 +85,7 @@ class TestGemStreamUI < Gem::TestCase
 
   def test_ask_yes_no_no_tty_with_default
     skip 'TTY handling is broken on windows' if
-      Gem.win_platform? unless RUBY_VERSION > '1.9.2'
+      Gem.win_platform? && RUBY_VERSION <= '1.9.2'
 
     @in.tty = false
 
@@ -100,7 +100,7 @@ class TestGemStreamUI < Gem::TestCase
 
   def test_ask_yes_no_no_tty_without_default
     skip 'TTY handling is broken on windows' if
-      Gem.win_platform? unless RUBY_VERSION > '1.9.2'
+      Gem.win_platform? && RUBY_VERSION <= '1.9.2'
 
     @in.tty = false
 
diff --git a/test/rubygems/test_gem_stub_specification.rb b/test/rubygems/test_gem_stub_specification.rb
index 53b9dab02d..43680265c7 100644
--- a/test/rubygems/test_gem_stub_specification.rb
+++ b/test/rubygems/test_gem_stub_specification.rb
@@ -110,6 +110,18 @@ class TestStubSpecification < Gem::TestCase
     assert_equal code_rb, stub.matches_for_glob('code*').first
   end
 
+  def test_matches_for_glob_with_bundler_inline
+    stub = stub_with_extension
+    code_rb = File.join stub.gem_dir, 'lib', 'code.rb'
+    FileUtils.mkdir_p File.dirname code_rb
+    FileUtils.touch code_rb
+
+    stub.stub(:raw_require_paths, nil) do
+      assert_equal code_rb, stub.matches_for_glob('code*').first
+    end
+  end
+
+
   def test_missing_extensions_eh
     stub = stub_with_extension do |s|
       extconf_rb = File.join s.gem_dir, s.extensions.first