diff --git a/pageindex/page_index.py b/pageindex/page_index.py
index 9004309fb..7f396aa54 100644
--- a/pageindex/page_index.py
+++ b/pageindex/page_index.py
@@ -414,6 +414,15 @@ def calculate_page_offset(pairs):
     return most_common
 
 def add_page_offset_to_toc_json(data, offset):
+    """Apply a page offset to convert TOC page numbers to physical indices.
+
+    When ``offset`` is ``None`` (e.g. because no matching title/page pairs
+    were found in the document), the function returns ``data`` unchanged
+    rather than crashing with a ``TypeError``.  Callers should handle the
+    resulting items-without-``physical_index`` through ``process_none_page_numbers``.
+    """
+    if offset is None:
+        return data
     for i in range(len(data)):
         if data[i].get('page') is not None and isinstance(data[i]['page'], int):
             data[i]['physical_index'] = data[i]['page'] + offset
@@ -654,18 +663,22 @@ def process_toc_with_page_numbers(toc_content, toc_page_list, page_list, toc_che
 
 ##check if needed to process none page numbers
 def process_none_page_numbers(toc_items, page_list, start_index=1, model=None):
+    end_index = len(page_list) + start_index - 1
     for i, item in enumerate(toc_items):
         if "physical_index" not in item:
             # logger.info(f"fix item: {item}")
             # Find previous physical_index
-            prev_physical_index = 0  # Default if no previous item exists
+            prev_physical_index = start_index  # Default: start of document
             for j in range(i - 1, -1, -1):
                 if toc_items[j].get('physical_index') is not None:
                     prev_physical_index = toc_items[j]['physical_index']
                     break
             
-            # Find next physical_index
-            next_physical_index = -1  # Default if no next item exists
+            # Find next physical_index.
+            # Default is end_index (last page of document) so that the last
+            # TOC item — which has no successor — still gets a valid search
+            # window instead of an empty range(prev, 0).
+            next_physical_index = end_index
             for j in range(i + 1, len(toc_items)):
                 if toc_items[j].get('physical_index') is not None:
                     next_physical_index = toc_items[j]['physical_index']
diff --git a/tests/__init__.py b/tests/__init__.py
new file mode 100644
index 000000000..e69de29bb
diff --git a/tests/test_toc_offset_and_page_range.py b/tests/test_toc_offset_and_page_range.py
new file mode 100644
index 000000000..4c58de84f
--- /dev/null
+++ b/tests/test_toc_offset_and_page_range.py
@@ -0,0 +1,220 @@
+"""
+Tests for two related bugs in TOC processing:
+
+Bug 1 — add_page_offset_to_toc_json crashes with TypeError when offset is None.
+    Root cause: calculate_page_offset() returns None when no title/page pairs can be
+    matched (e.g. the visible TOC pages don't overlap with the first N pages of content).
+    add_page_offset_to_toc_json() then tried ``data[i]['page'] + None``, raising TypeError.
+
+Bug 2 — process_none_page_numbers produces an empty page-content window for the *last*
+    TOC item when it has no physical_index.
+    Root cause: ``next_physical_index`` defaulted to ``-1`` (meaning "no next item"),
+    and ``range(prev, -1 + 1)`` == ``range(prev, 0)`` is always empty.  The LLM was
+    called with an empty string and could not locate the section.
+    Secondary: ``prev_physical_index`` defaulted to ``0``, which produces list_index ``-1``
+    and silently skips the first page (bounds check catches it, but page 1 is excluded).
+"""
+import copy
+import pytest
+
+from pageindex.page_index import (
+    add_page_offset_to_toc_json,
+    calculate_page_offset,
+    process_none_page_numbers,
+)
+
+
+# ---------------------------------------------------------------------------
+# Bug 1: add_page_offset_to_toc_json with None offset
+# ---------------------------------------------------------------------------
+
+class TestAddPageOffsetToTocJson:
+    """Covers the None-offset guard added to add_page_offset_to_toc_json."""
+
+    def test_none_offset_returns_data_unchanged(self):
+        """When offset is None the input list must be returned unmodified."""
+        data = [
+            {"structure": "1", "title": "Introduction", "page": 5},
+            {"structure": "2", "title": "Methods", "page": 10},
+        ]
+        original = copy.deepcopy(data)
+        result = add_page_offset_to_toc_json(data, None)
+        assert result == original, "Data should be unchanged when offset is None"
+
+    def test_none_offset_no_crash(self):
+        """No exception must be raised when offset is None."""
+        data = [{"structure": "1", "title": "Intro", "page": 3}]
+        try:
+            add_page_offset_to_toc_json(data, None)
+        except TypeError as exc:
+            pytest.fail(f"TypeError raised with None offset: {exc}")
+
+    def test_integer_offset_applied_correctly(self):
+        """A valid integer offset must still compute physical_index = page + offset."""
+        data = [
+            {"structure": "1", "title": "Intro", "page": 5},
+            {"structure": "2", "title": "Methods", "page": 10},
+        ]
+        result = add_page_offset_to_toc_json(data, 3)
+        assert result[0]["physical_index"] == 8
+        assert result[1]["physical_index"] == 13
+        assert "page" not in result[0]
+        assert "page" not in result[1]
+
+    def test_zero_offset_applied_correctly(self):
+        """Offset of 0 means page number == physical_index."""
+        data = [{"structure": "1", "title": "Intro", "page": 7}]
+        result = add_page_offset_to_toc_json(data, 0)
+        assert result[0]["physical_index"] == 7
+        assert "page" not in result[0]
+
+    def test_negative_offset_applied_correctly(self):
+        """Negative offsets (e.g. roman-numeral front matter) must work."""
+        data = [{"structure": "1", "title": "Chapter 1", "page": 10}]
+        result = add_page_offset_to_toc_json(data, -2)
+        assert result[0]["physical_index"] == 8
+
+    def test_none_page_value_skipped(self):
+        """Items with page=None must not be modified even with a valid offset."""
+        data = [{"structure": "1", "title": "Unknown", "page": None}]
+        result = add_page_offset_to_toc_json(data, 3)
+        assert result[0].get("page") is None
+        assert "physical_index" not in result[0]
+
+    def test_item_without_page_key_skipped(self):
+        """Items that already have a physical_index (no 'page' key) are untouched."""
+        data = [{"structure": "1", "title": "Intro", "physical_index": 5}]
+        result = add_page_offset_to_toc_json(data, 3)
+        assert result[0]["physical_index"] == 5  # unchanged
+
+    def test_empty_list_none_offset(self):
+        """Empty input list with None offset must return empty list."""
+        assert add_page_offset_to_toc_json([], None) == []
+
+    def test_empty_list_integer_offset(self):
+        """Empty input list with integer offset must return empty list."""
+        assert add_page_offset_to_toc_json([], 5) == []
+
+    def test_calculate_page_offset_returns_none_for_empty_pairs(self):
+        """calculate_page_offset([]) must return None (documents the contract)."""
+        assert calculate_page_offset([]) is None
+
+    def test_pipeline_none_offset_does_not_crash(self):
+        """
+        End-to-end simulation: matching_pairs empty → offset None →
+        add_page_offset_to_toc_json must not crash.
+        """
+        toc = [
+            {"structure": "1", "title": "Intro", "page": 1},
+            {"structure": "2", "title": "Methods", "page": 5},
+        ]
+        pairs = []  # No matches found → offset will be None
+        offset = calculate_page_offset(pairs)
+        assert offset is None
+        # Must not raise
+        result = add_page_offset_to_toc_json(toc, offset)
+        # All items still have 'page' key (unchanged)
+        assert all("page" in item for item in result)
+
+
+# ---------------------------------------------------------------------------
+# Bug 2: process_none_page_numbers — empty range for last/first items
+# ---------------------------------------------------------------------------
+
+class TestProcessNonePageNumbers:
+    """Covers the empty-range bug in process_none_page_numbers."""
+
+    @staticmethod
+    def _make_page_list(n):
+        """Return a synthetic page_list of length n."""
+        return [(f"Content of page {i + 1}", 50) for i in range(n)]
+
+    def test_last_item_gets_non_empty_range(self):
+        """
+        The *last* TOC item (no successor) used to produce range(prev, 0) which is
+        always empty — the LLM received an empty string.  After the fix, the default
+        next_physical_index is end_index = len(page_list) + start_index - 1.
+        """
+        # Simulate: the last entry has no physical_index yet
+        # We can verify the window by checking that page_contents is non-empty
+        # when we manually replicate the loop logic from process_none_page_numbers.
+        page_list = self._make_page_list(5)
+        start_index = 1
+        end_index = len(page_list) + start_index - 1  # = 5
+
+        # Scenario: item at index 1 has no physical_index, no next item
+        prev_physical_index = 2  # from item at index 0
+        next_physical_index = end_index  # new default
+
+        page_range = list(range(prev_physical_index, next_physical_index + 1))
+        assert page_range == [2, 3, 4, 5], (
+            f"Expected [2,3,4,5] but got {page_range} — last item would get empty context"
+        )
+
+    def test_first_item_prev_default_is_start_index(self):
+        """
+        The *first* TOC item (no predecessor) used to default prev_physical_index to 0.
+        With start_index=1, list_index = 0 - 1 = -1, which is silently skipped by the
+        bounds check.  While the effective window was the same (page 1 still appeared
+        due to the subsequent loop), the new default start_index avoids computing
+        a negative list_index entirely — a cleaner, less error-prone starting point.
+        """
+        start_index = 1
+
+        # Old code attempted page 0, list_index = 0 - 1 = -1, bounds check skips it.
+        # Effective window started at page 1 anyway.
+        old_attempted_list_index = 0 - start_index  # = -1
+        assert old_attempted_list_index < 0, "Old code produced list_index=-1 (bounds-checked away)"
+
+        # New code: prev = start_index = 1, list_index = 1 - 1 = 0 (valid)
+        new_first_list_index = start_index - start_index  # = 0
+        assert new_first_list_index == 0, "New code starts at list_index=0 (no negative index attempted)"
+
+    def test_single_page_document_last_item(self):
+        """A 1-page document whose sole TOC item has no physical_index should get range [1,1]."""
+        page_list = self._make_page_list(1)
+        start_index = 1
+        end_index = 1
+
+        prev_physical_index = start_index   # new default (no predecessor)
+        next_physical_index = end_index     # new default (no successor)
+
+        page_range = list(range(prev_physical_index, next_physical_index + 1))
+        assert page_range == [1]
+
+    def test_middle_item_range_uses_neighbors(self):
+        """A middle item should still use actual neighbor physical indices."""
+        # item at index 1 (between items 0 and 2 with known physical_index)
+        page_list = self._make_page_list(10)
+        start_index = 1
+        prev_physical_index = 3   # from item 0
+        next_physical_index = 7   # from item 2
+
+        page_range = list(range(prev_physical_index, next_physical_index + 1))
+        assert page_range == [3, 4, 5, 6, 7]
+
+    def test_regression_old_next_default_minus_one(self):
+        """
+        Regression: range(prev, -1 + 1) == range(prev, 0) must be empty.
+        Confirms the old bug and validates the fix direction.
+        """
+        prev = 3
+        old_next = -1  # old default
+        new_next = 5   # new default (end_index for a 5-page doc)
+
+        assert list(range(prev, old_next + 1)) == [], "Old code produced empty range"
+        assert list(range(prev, new_next + 1)) == [3, 4, 5], "New code produces valid range"
+
+    def test_all_items_have_physical_index_no_op(self):
+        """When every item already has physical_index, function must return unchanged."""
+        page_list = self._make_page_list(5)
+        toc_items = [
+            {"structure": "1", "title": "Intro", "physical_index": 1},
+            {"structure": "2", "title": "Methods", "physical_index": 3},
+            {"structure": "3", "title": "Results", "physical_index": 5},
+        ]
+        original = copy.deepcopy(toc_items)
+        result = process_none_page_numbers(toc_items, page_list)
+        # physical_index values must remain the same (no LLM called, no changes)
+        for orig, res in zip(original, result):
+            assert res["physical_index"] == orig["physical_index"]