diff --git a/lib/rdoc/markup/to_html.rb b/lib/rdoc/markup/to_html.rb
index f3dd96e157..d3bb8af835 100644
--- a/lib/rdoc/markup/to_html.rb
+++ b/lib/rdoc/markup/to_html.rb
@@ -357,7 +357,7 @@ class RDoc::Markup::ToHtml < RDoc::Markup::Formatter
        url =~ /\.(gif|png|jpg|jpeg|bmp)$/ then
       "<img src=\"#{url}\" />"
     else
-      if scheme != 'link' and %r%\A((?!https?:).*/)([^/]+)\.(rb|rdoc|md)(?=\z|#)%i =~ url
+      if scheme != 'link' and %r%\A((?!https?:)(?:[^/#]*/)*+)([^/#]+)\.(rb|rdoc|md)(?=\z|#)%i =~ url
         url = "#$1#{$2.tr('.', '_')}_#$3.html#$'"
       end
 
diff --git a/test/rdoc/test_rdoc_markup_to_html.rb b/test/rdoc/test_rdoc_markup_to_html.rb
index aa36fb77c4..342cf71082 100644
--- a/test/rdoc/test_rdoc_markup_to_html.rb
+++ b/test/rdoc/test_rdoc_markup_to_html.rb
@@ -739,6 +739,8 @@ EXPECTED
   end
 
   def test_gen_url_rdoc_file
+    assert_equal '<a href="example_rdoc.html">example</a>',
+                 @to.gen_url('example.rdoc', 'example')
     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>',
@@ -750,6 +752,8 @@ EXPECTED
   end
 
   def test_gen_url_md_file
+    assert_equal '<a href="example_md.html">example</a>',
+                 @to.gen_url('example.md', 'example')
     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>',
@@ -761,6 +765,8 @@ EXPECTED
   end
 
   def test_gen_url_rb_file
+    assert_equal '<a href="example_rb.html">example</a>',
+                 @to.gen_url('example.rb', 'example')
     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>',