1 files changed, 116 insertions, 3 deletions

diff --git a/test/ruby/test_autoload.rb b/test/ruby/test_autoload.rb
index ca3e3d5f7f..de08be96e4 100644
--- a/test/ruby/test_autoload.rb
+++ b/test/ruby/test_autoload.rb
@@ -224,11 +224,18 @@ p Foo::Bar
     Kernel.module_eval do
       alias old_require require
     end
+    Ruby::Box.module_eval do
+      alias old_require require
+    end
     called_with = []
     Kernel.send :define_method, :require do |path|
       called_with << path
       old_require path
     end
+    Ruby::Box.send :define_method, :require do |path|
+      called_with << path
+      old_require path
+    end
     yield called_with
   ensure
     Kernel.module_eval do
@@ -236,6 +243,11 @@ p Foo::Bar
       alias require old_require
       undef old_require
     end
+    Ruby::Box.module_eval do
+      undef require
+      alias require old_require
+      undef old_require
+    end
   end
 
   def test_require_implemented_in_ruby_is_called
@@ -249,7 +261,8 @@ p Foo::Bar
         ensure
           remove_autoload_constant
         end
-        assert_equal [file.path], called_with
+        # .dup to prevent breaking called_with by autoloading pp, etc
+        assert_equal [file.path], called_with.dup
       }
     end
   end
@@ -267,7 +280,8 @@ p Foo::Bar
           ensure
             remove_autoload_constant
           end
-          assert_equal [a.path, b.path], called_with
+          # .dup to prevent breaking called_with by autoloading pp, etc
+          assert_equal [a.path, b.path], called_with.dup
         end
       end
     end
@@ -560,7 +574,7 @@ p Foo::Bar
       autoload_path = File.join(tmpdir, "autoload_parallel_race.rb")
       File.write(autoload_path, 'module Foo; end; module Bar; end')
 
-      assert_separately([], <<-RUBY, timeout: 100)
+      assert_ruby_status([], <<-RUBY, timeout: 100)
         autoload_path = #{File.realpath(autoload_path).inspect}
 
         # This should work with no errors or failures.
@@ -599,4 +613,103 @@ p Foo::Bar
       RUBY
     end
   end
+
+  def test_autoload_relative_toplevel
+    Dir.mktmpdir('autoload_relative') do |tmpdir|
+      main_file = File.join(tmpdir, 'main.rb')
+      module_file = File.join(tmpdir, 'test_module.rb')
+
+      File.write(module_file, <<-RUBY)
+        module AutoloadRelativeTest
+          VERSION = '1.0'
+        end
+      RUBY
+
+      File.write(main_file, <<-RUBY)
+        autoload_relative :AutoloadRelativeTest, 'test_module.rb'
+        puts AutoloadRelativeTest::VERSION
+      RUBY
+
+      assert_in_out_err([main_file], '', ['1.0'], [])
+    end
+  end
+
+  def test_autoload_relative_module_level
+    Dir.mktmpdir('autoload_relative') do |tmpdir|
+      main_file = File.join(tmpdir, 'main_mod.rb')
+      module_file = File.join(tmpdir, 'nested_module.rb')
+
+      File.write(module_file, <<-RUBY)
+        module Container
+          module NestedModule
+            MSG = 'loaded'
+          end
+        end
+      RUBY
+
+      File.write(main_file, <<-RUBY)
+        module Container
+          autoload_relative :NestedModule, 'nested_module.rb'
+        end
+        puts Container::NestedModule::MSG
+      RUBY
+
+      assert_in_out_err([main_file], '', ['loaded'], [])
+    end
+  end
+
+  def test_autoload_relative_query
+    Dir.mktmpdir('autoload_relative') do |tmpdir|
+      main_file = File.join(tmpdir, 'query_test.rb')
+      module_file = File.join(tmpdir, 'query_module.rb')
+
+      File.write(module_file, 'module QueryModule; end')
+
+      File.write(main_file, <<-RUBY)
+        autoload_relative :QueryModule, 'query_module.rb'
+        path = autoload?(:QueryModule)
+        # Use realpath for comparison to handle symlinks (e.g., /var -> /private/var on macOS)
+        real_tmpdir = File.realpath('#{tmpdir}')
+        puts path.start_with?(real_tmpdir) && path.end_with?('query_module.rb')
+      RUBY
+
+      assert_in_out_err([main_file], '', ['true'], [])
+    end
+  end
+
+  def test_autoload_relative_nested_directory
+    Dir.mktmpdir('autoload_relative') do |tmpdir|
+      nested_dir = File.join(tmpdir, 'nested')
+      Dir.mkdir(nested_dir)
+
+      main_file = File.join(tmpdir, 'nested_test.rb')
+      module_file = File.join(nested_dir, 'deep_module.rb')
+
+      File.write(module_file, 'module DeepModule; VALUE = 42; end')
+
+      File.write(main_file, <<-RUBY)
+        autoload_relative :DeepModule, 'nested/deep_module.rb'
+        puts DeepModule::VALUE
+      RUBY
+
+      assert_in_out_err([main_file], '', ['42'], [])
+    end
+  end
+
+  def test_autoload_relative_no_basepath
+    # Test that autoload_relative raises an error when called from eval without file context
+    assert_raise(LoadError) do
+      eval('autoload_relative :TestConst, "test.rb"')
+    end
+  end
+
+  private
+
+  def assert_separately(*args, **kwargs)
+    super(*args, timeout: 60, **kwargs)
+  end
+
+  def assert_ruby_status(*args, **kwargs)
+    super(*args, timeout: 60, **kwargs)
+  end
 end