diff --git a/CHANGELOG.md b/CHANGELOG.md
index ae876ef8..4151bca2 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,7 @@
 
 - Project prepared to be installed with `pip install`, so it can be reused in 
   the repository https://github.com/canonical/gatekeeper-repo-test
+- Added support for navigation table with hierarchy jumps of more than 1 level
 
 ## [v0.9.0] - 2024-04-04
 
diff --git a/src-docs/index.py.md b/src-docs/index.py.md
index 54059347..083a0e6d 100644
--- a/src-docs/index.py.md
+++ b/src-docs/index.py.md
@@ -123,7 +123,7 @@ Classify the type of a reference.
 
 ---
 
-<a href="../src/gatekeeper/index.py#L413"><img align="right" style="float:right;" src="https://img.shields.io/badge/-source-cccccc?style=flat-square"></a>
+<a href="../src/gatekeeper/index.py#L414"><img align="right" style="float:right;" src="https://img.shields.io/badge/-source-cccccc?style=flat-square"></a>
 
 ## <kbd>function</kbd> `get_contents`
 
diff --git a/src/gatekeeper/index.py b/src/gatekeeper/index.py
index 5dbf1485..087aaf15 100644
--- a/src/gatekeeper/index.py
+++ b/src/gatekeeper/index.py
@@ -370,6 +370,7 @@ def _calculate_contents_hierarchy(
             hierarchy = hierarchy - 1
             parent = parents.pop()
             aggregate_dir = Path(parent.reference_value).parent
+            continue
 
         _check_contents_item(
             item=item,
diff --git a/tests/unit/test_index_contents_hierarchy.py b/tests/unit/test_index_contents_hierarchy.py
index 6368fdde..c4aba6ec 100644
--- a/tests/unit/test_index_contents_hierarchy.py
+++ b/tests/unit/test_index_contents_hierarchy.py
@@ -266,6 +266,50 @@ def _test__calculate_contents_hierarchy_invalid_parameters():
             ("not immediately within", "directory", value_1, repr(item)),
             id="directory in wrong directory",
         ),
+        pytest.param(
+            (
+                item_1 := factories.IndexParsedListItemFactory(
+                    whitespace_count=0, reference_value=(value_1 := "dir1")
+                ),
+                item_2 := factories.IndexParsedListItemFactory(
+                    whitespace_count=1, reference_value=(value_2 := f"{value_1}/dir2")
+                ),
+                item_3 := factories.IndexParsedListItemFactory(
+                    whitespace_count=2, reference_value=(value_3 := f"{value_2}/file3.md")
+                ),
+                item_4 := factories.IndexParsedListItemFactory(
+                    whitespace_count=0, reference_value=(value_4 := "dir4")
+                ),   
+            ),
+            ("dir", "dir", "file", "dir"),
+            (
+                factories.IndexContentsListItemFactory(
+                    hierarchy=1,
+                    reference_title=item_1.reference_title,
+                    reference_value=value_1,
+                    rank=item_1.rank,
+                ),
+                factories.IndexContentsListItemFactory(
+                    hierarchy=2,
+                    reference_title=item_2.reference_title,
+                    reference_value=value_2,
+                    rank=item_2.rank,
+                ),
+                factories.IndexContentsListItemFactory(
+                    hierarchy=3,
+                    reference_title=item_3.reference_title,
+                    reference_value=value_3,
+                    rank=item_3.rank,
+                ),
+                factories.IndexContentsListItemFactory(
+                    hierarchy=1,
+                    reference_title=item_4.reference_title,
+                    reference_value=value_4,
+                    rank=item_4.rank,
+                ),
+            ),
+            id="dir following an item nested more than once",
+        )
     ]