diff --git a/pageindex/page_index_classic.py b/pageindex/page_index_classic.py
index 446e8893b..29d8117c4 100644
--- a/pageindex/page_index_classic.py
+++ b/pageindex/page_index_classic.py
@@ -528,7 +528,8 @@ def page_list_to_group_text(page_contents, token_lengths, max_tokens=20000, over
     average_tokens_per_part = math.ceil(((num_tokens / expected_parts_num) + max_tokens) / 2)
     
     for i, (page_content, page_tokens) in enumerate(zip(page_contents, token_lengths)):
-        if current_token_count + page_tokens > average_tokens_per_part:
+        # without the guard, an oversized first page flushes an empty chunk
+        if current_subset and current_token_count + page_tokens > average_tokens_per_part:
 
             subsets.append(''.join(current_subset))
             # Start new subset from overlap if specified
diff --git a/tests/test_page_index.py b/tests/test_page_index.py
index da69a9a79..4422d5c1c 100644
--- a/tests/test_page_index.py
+++ b/tests/test_page_index.py
@@ -3,6 +3,7 @@
 
 from pageindex.page_index_classic import (
     _secure_doc_text,
+    page_list_to_group_text,
     process_no_toc,
     process_toc_no_page_numbers,
 )
@@ -65,5 +66,39 @@ def test_secure_doc_text_neutralizes_document_delimiters(self):
         self.assertIn("<physical_index_1>", wrapped)
 
 
+class PageListToGroupTextTest(unittest.TestCase):
+    PAGES = ["PAGE-A", "PAGE-B", "PAGE-C"]
+
+    def test_oversized_first_page_does_not_emit_an_empty_chunk(self):
+        chunks = page_list_to_group_text(
+            self.PAGES, [60000, 500, 500], max_tokens=20000
+        )
+
+        self.assertNotIn("", chunks)
+
+    def test_every_page_survives_an_oversized_first_page(self):
+        chunks = page_list_to_group_text(
+            self.PAGES, [60000, 500, 500], max_tokens=20000
+        )
+
+        joined = "".join(chunks)
+        for page in self.PAGES:
+            self.assertIn(page, joined)
+
+    def test_oversized_middle_page_is_unaffected(self):
+        chunks = page_list_to_group_text(
+            self.PAGES, [100, 60000, 100], max_tokens=20000
+        )
+
+        self.assertNotIn("", chunks)
+
+    def test_document_under_the_limit_stays_one_chunk(self):
+        chunks = page_list_to_group_text(
+            self.PAGES, [100, 100, 100], max_tokens=20000
+        )
+
+        self.assertEqual(chunks, ["PAGE-APAGE-BPAGE-C"])
+
+
 if __name__ == "__main__":
     unittest.main()