diff --git a/org_rw/org_rw.py b/org_rw/org_rw.py
index 90ff004..c40f0e4 100644
--- a/org_rw/org_rw.py
+++ b/org_rw/org_rw.py
@@ -464,8 +464,9 @@ class Headline:
                         if isinstance(c, dom.ListItem)
                     ]
 
-                    if ((len(list_children) > 0)
-                        and (len(list_children[-1].orig.indentation)
+                    if (len(list_children) == 0):
+                        break
+                    if ((len(list_children[-1].orig.indentation)
                              <= len(line.indentation))):
                         # No more breaking out of lists, it's indentation
                         # is less than ours
diff --git a/tests/11-nested-lists.org b/tests/11-nested-lists.org
new file mode 100644
index 0000000..a4a8632
--- /dev/null
+++ b/tests/11-nested-lists.org
@@ -0,0 +1,16 @@
+#+TITLE: 11-Nested lists
+#+DESCRIPTION: Simple org file to test nested lists
+#+TODO: TODO(t) PAUSED(p) |  DONE(d)
+
+* Nested lists
+  :PROPERTIES:
+  :ID:       11-nested-lists
+  :CREATED:  [2020-01-01 Wed 01:01]
+  :END:
+  - 1
+    - 1.1
+    - 1.2
+  - 2
+    - 2.1
+    - 2.2
+  - 3
diff --git a/tests/test_org.py b/tests/test_org.py
index 1255067..2f4200d 100644
--- a/tests/test_org.py
+++ b/tests/test_org.py
@@ -724,6 +724,39 @@ class TestSerde(unittest.TestCase):
         self.assertTrue(len(non_props) == 1,
                         'Expected <List>, with only (1) element')
 
+    def test_nested_lists_html_file_11(self):
+        with open(os.path.join(DIR, "11-nested-lists.org")) as f:
+            doc = load(f)
+
+        hl = doc.getTopHeadlines()[0]
+
+        tree = hl.as_dom()
+        non_props = [
+            item
+            for item in tree
+            if not isinstance(item, dom.PropertyDrawerNode)
+        ]
+        print_tree(non_props)
+        self.assertTrue((len(non_props) == 1) and (isinstance(non_props[0], dom.ListGroupNode)),
+                        'Expected only <List> as top level')
+
+        dom_list = non_props[0]
+        children = dom_list.children
+        self.assertTrue(len(children) == 5, 'Expected 5 items inside <List>, 3 texts and 2 sublists')
+
+        # Assert texts
+        self.assertEqual(children[0].content, ['1'])
+        self.assertEqual(children[2].content, ['2'])
+        self.assertEqual(children[4].content[0], '3')  # Might be ['3', '\n'] but shouldn't be a breaking change
+
+        # Assert lists
+        self.assertTrue(isinstance(children[1], dom.ListGroupNode), 'Expected sublist inside "1"')
+        self.assertEqual(children[1].children[0].content, ['1.1'])
+        self.assertEqual(children[1].children[1].content, ['1.2'])
+        self.assertTrue(isinstance(children[3], dom.ListGroupNode), 'Expected sublist inside "2"')
+        self.assertEqual(children[3].children[0].content, ['2.1'])
+        self.assertEqual(children[3].children[1].content, ['2.2'])
+
 
 def print_tree(tree, indentation=0, headline=None):
     for element in tree: