diff --git a/docling/utils/pdf_outline.py b/docling/utils/pdf_outline.py
index cab458eaf1..5bfa2ede00 100644
--- a/docling/utils/pdf_outline.py
+++ b/docling/utils/pdf_outline.py
@@ -163,12 +163,18 @@ def extract_outline_from_docling_parse(
 
     items: list[_PdfOutlineItem] = []
 
-    def _walk(node: PdfTableOfContents, level: int) -> None:
-        for child in node.children or []:
-            title = (child.text or child.orig or "").strip()
-            if title:
-                items.append(_PdfOutlineItem(title=title, level=level))
-            _walk(child, level + 1)
-
-    _walk(toc, 0)
+    # Iterative pre-order depth-first walk via an explicit stack, avoiding Python's
+    # call-stack recursion limit. Some large real-world documents (technical manuals,
+    # legal filings) legitimately nest headings hundreds of levels deep, and malformed
+    # PDFs can nest further still; a naive recursive walk here raises RecursionError.
+    stack: list[tuple[PdfTableOfContents, int]] = [
+        (child, 0) for child in reversed(toc.children or [])
+    ]
+    while stack:
+        node, level = stack.pop()
+        title = (node.text or node.orig or "").strip()
+        if title:
+            items.append(_PdfOutlineItem(title=title, level=level))
+        stack.extend((child, level + 1) for child in reversed(node.children or []))
+
     return items
diff --git a/tests/test_pdf_outline.py b/tests/test_pdf_outline.py
new file mode 100644
index 0000000000..8fdc9003fa
--- /dev/null
+++ b/tests/test_pdf_outline.py
@@ -0,0 +1,111 @@
+from docling.utils.pdf_outline import extract_outline_from_docling_parse
+
+
+class _MockTocNode:
+    """Duck-typed stand-in for docling_parse's PdfTableOfContents node.
+
+    extract_outline_from_docling_parse only accesses .children, .text, and
+    .orig on each node, so a lightweight mock is sufficient and avoids a
+    dependency on constructing a real PDF with an outline.
+    """
+
+    def __init__(self, text="", children=None):
+        self.text = text
+        self.orig = text
+        self.children = children or []
+
+
+class _MockPdfDocument:
+    """Duck-typed stand-in for docling_parse's PdfDocument, exposing only
+    the one method extract_outline_from_docling_parse calls."""
+
+    def __init__(self, toc_root):
+        self._toc_root = toc_root
+
+    def get_table_of_contents(self):
+        return self._toc_root
+
+
+def _build_chain(depth: int) -> _MockTocNode:
+    """Build a linear chain of nested nodes depth levels deep:
+    root -> child -> child -> ... (depth - 1 named children below root)."""
+    root = _MockTocNode("level_0")
+    current = root
+    for i in range(1, depth):
+        child = _MockTocNode(f"level_{i}")
+        current.children = [child]
+        current = child
+    return root
+
+
+def test_outline_no_toc_returns_empty_list():
+    class _NoTocDoc:
+        def get_table_of_contents(self):
+            return None
+
+    assert extract_outline_from_docling_parse(_NoTocDoc()) == []
+
+
+def test_outline_flat_structure():
+    root = _MockTocNode(
+        "root",
+        children=[_MockTocNode("First"), _MockTocNode("Second"), _MockTocNode("Third")],
+    )
+    items = extract_outline_from_docling_parse(_MockPdfDocument(root))
+    assert [(item.title, item.level) for item in items] == [
+        ("First", 0),
+        ("Second", 0),
+        ("Third", 0),
+    ]
+
+
+def test_outline_nested_structure_preserves_order_and_levels():
+    root = _MockTocNode(
+        "root",
+        children=[
+            _MockTocNode(
+                "Chapter 1",
+                children=[_MockTocNode("1.1"), _MockTocNode("1.2")],
+            ),
+            _MockTocNode("Chapter 2"),
+        ],
+    )
+    items = extract_outline_from_docling_parse(_MockPdfDocument(root))
+    assert [(item.title, item.level) for item in items] == [
+        ("Chapter 1", 0),
+        ("1.1", 1),
+        ("1.2", 1),
+        ("Chapter 2", 0),
+    ]
+
+
+def test_outline_blank_and_whitespace_titles_are_excluded():
+    root = _MockTocNode(
+        "root",
+        children=[
+            _MockTocNode(""),
+            _MockTocNode("   "),
+            _MockTocNode("  Real Title  "),
+        ],
+    )
+    items = extract_outline_from_docling_parse(_MockPdfDocument(root))
+    assert [(item.title, item.level) for item in items] == [("Real Title", 0)]
+
+
+def test_outline_deep_chain_does_not_raise_recursion_error():
+    """Regression test: a naive recursive walk over the outline tree raises
+    RecursionError once the tree is deeper than Python's call-stack limit
+    (default 1000). Large real-world documents can legitimately have this
+    many nested heading levels. Use a depth well past the default limit to
+    make sure this is actually exercised regardless of interpreter
+    settings."""
+    depth = 5000
+    root = _build_chain(depth)
+
+    items = extract_outline_from_docling_parse(_MockPdfDocument(root))
+
+    assert len(items) == depth - 1
+    assert items[0].title == "level_1"
+    assert items[0].level == 0
+    assert items[-1].title == f"level_{depth - 1}"
+    assert items[-1].level == depth - 2