diff --git a/lib/rdoc/markup/to_html.rb b/lib/rdoc/markup/to_html.rb
index e2a00bd8a1..8ae4dd4720 100644
--- a/lib/rdoc/markup/to_html.rb
+++ b/lib/rdoc/markup/to_html.rb
@@ -357,6 +357,10 @@ def gen_url url, text
        url =~ /\.(gif|png|jpg|jpeg|bmp)$/ then
       "<img src=\"#{url}\" />"
     else
+      if scheme != 'link' and /\.(?:rb|rdoc|md)\z/i =~ url
+        url = url.sub(%r%\A([./]*)(.*)\z%) { "#$1#{$2.tr('.', '_')}.html" }
+      end
+
       text = text.sub %r%^#{scheme}:/*%i, ''
       text = text.sub %r%^[*\^](\d+)$%,   '\1'
 
diff --git a/test/rdoc/test_rdoc_markup_to_html.rb b/test/rdoc/test_rdoc_markup_to_html.rb
index 0b25f462ae..29da968abc 100644
--- a/test/rdoc/test_rdoc_markup_to_html.rb
+++ b/test/rdoc/test_rdoc_markup_to_html.rb
@@ -738,6 +738,27 @@ def test_gen_url_ssl_image_url
     assert_equal '<img src="https://example.com/image.png" />', @to.gen_url('https://example.com/image.png', 'ignored')
   end
 
+  def test_gen_url_rdoc_file
+    assert_equal '<a href="doc/example_rdoc.html">example</a>',
+                 @to.gen_url('doc/example.rdoc', 'example')
+    assert_equal '<a href="../ex_doc/example_rdoc.html">example</a>',
+                 @to.gen_url('../ex.doc/example.rdoc', 'example')
+  end
+
+  def test_gen_url_md_file
+    assert_equal '<a href="doc/example_md.html">example</a>',
+                 @to.gen_url('doc/example.md', 'example')
+    assert_equal '<a href="../ex_doc/example_md.html">example</a>',
+                 @to.gen_url('../ex.doc/example.md', 'example')
+  end
+
+  def test_gen_url_rb_file
+    assert_equal '<a href="doc/example_rb.html">example</a>',
+                 @to.gen_url('doc/example.rb', 'example')
+    assert_equal '<a href="../ex_doc/example_rb.html">example</a>',
+                 @to.gen_url('../ex.doc/example.rb', 'example')
+  end
+
   def test_handle_regexp_HYPERLINK_link
     target = RDoc::Markup::RegexpHandling.new 0, 'link:README.txt'
 
diff --git a/test/rdoc/test_rdoc_top_level.rb b/test/rdoc/test_rdoc_top_level.rb
index e396791ab8..a954fde981 100644
--- a/test/rdoc/test_rdoc_top_level.rb
+++ b/test/rdoc/test_rdoc_top_level.rb
@@ -157,6 +157,9 @@ def test_hash
 
   def test_http_url
     assert_equal 'prefix/path/top_level_rb.html', @top_level.http_url('prefix')
+
+    other_level = @store.add_file 'path.other/level.rb'
+    assert_equal 'prefix/path_other/level_rb.html', other_level.http_url('prefix')
   end
 
   def test_last_modified