diff --git a/lib/redcloth3.rb b/lib/redcloth3.rb
index f6333b3fe..c91c61718 100644
--- a/lib/redcloth3.rb
+++ b/lib/redcloth3.rb
@@ -585,7 +585,7 @@ class RedCloth3 < String
                     last_line = line_id
                 end
                 if line_id - last_line > 1 or line_id == lines.length - 1
-                    depth.delete_if do |v|
+                    while v = depth.pop
                         lines[last_line] << "</li>\n\t</#{ lT( v ) }l>"
                     end
                 end
diff --git a/test/unit/lib/redmine/wiki_formatting/textile_formatter_test.rb b/test/unit/lib/redmine/wiki_formatting/textile_formatter_test.rb
index 4253b7152..548a378b5 100644
--- a/test/unit/lib/redmine/wiki_formatting/textile_formatter_test.rb
+++ b/test/unit/lib/redmine/wiki_formatting/textile_formatter_test.rb
@@ -110,6 +110,36 @@ class Redmine::WikiFormatting::TextileFormatterTest < ActionView::TestCase
     )
   end
 
+  def test_nested_lists
+    raw = <<-RAW
+# Item 1
+# Item 2
+** Item 2a
+** Item 2b
+# Item 3
+** Item 3a
+RAW
+
+    expected = <<-EXPECTED
+<ol>
+  <li>Item 1</li>
+  <li>Item 2
+    <ul>
+      <li>Item 2a</li>
+      <li>Item 2b</li>
+    </ul>
+  </li>
+  <li>Item 3
+    <ul>
+      <li>Item 3a</li>
+    </ul>
+  </li>
+</ol>
+EXPECTED
+
+    assert_equal expected.gsub(%r{\s+}, ''), to_html(raw).gsub(%r{\s+}, '')
+  end
+
   def test_escaping
     assert_html_output(
       'this is a <script>'      => 'this is a &lt;script&gt;'