diff --git a/langextract/annotation.py b/langextract/annotation.py
index 4f0ec7b..0782d4b 100644
--- a/langextract/annotation.py
+++ b/langextract/annotation.py
@@ -357,13 +357,14 @@ def _annotate_documents_single_pass(
               "Completing annotation for document ID %s.",
               curr_document.document_id,
           )
+          doc_extractions = list(annotated_extractions)
           annotated_doc = data.AnnotatedDocument(
               document_id=curr_document.document_id,
-              extractions=annotated_extractions,
+              extractions=doc_extractions,
               text=curr_document.text,
           )
           yield annotated_doc
-          annotated_extractions.clear()
+          annotated_extractions = []  # Ensure next document gets a fresh list.
 
           curr_document = next(doc_iter, None)
           assert curr_document is not None, (
@@ -400,13 +401,15 @@ def _annotate_documents_single_pass(
       logging.info(
           "Finalizing annotation for document ID %s.", curr_document.document_id
       )
+      doc_extractions = list(annotated_extractions)
       annotated_doc = data.AnnotatedDocument(
           document_id=curr_document.document_id,
-          extractions=annotated_extractions,
+          extractions=doc_extractions,
           text=curr_document.text,
       )
 
       yield annotated_doc
+      annotated_extractions = []  # Fresh list prevents bleed into future docs.
 
     logging.info("Document annotation completed.")
 
diff --git a/tests/annotation_test.py b/tests/annotation_test.py
index 78df7dd..ce9d97c 100644
--- a/tests/annotation_test.py
+++ b/tests/annotation_test.py
@@ -742,6 +742,93 @@ def mock_infer_side_effect(batch_prompts, **kwargs):
 
     self.assertGreaterEqual(mock_language_model.infer.call_count, 0)
 
+  def test_annotate_documents_prevents_document_bleed(self):
+    mock_language_model = mock.Mock()
+    call_outputs = [
+        [types.ScoredOutput(score=1.0, output="DOC1")],
+        [types.ScoredOutput(score=1.0, output="DOC2")],
+    ]
+
+    def infer_side_effect(batch_prompts, **kwargs):
+      self.assertLen(batch_prompts, 1)
+      self.assertTrue(call_outputs)
+      outputs_for_call = call_outputs.pop(0)
+      return [list(outputs_for_call)]
+
+    mock_language_model.infer.side_effect = infer_side_effect
+
+    class _FakeResolver:
+
+      def resolve(self, llm_output, **kwargs):
+        if llm_output == "DOC1":
+          return [
+              data.Extraction(
+                  extraction_class="Person",
+                  extraction_text="Bob",
+              )
+          ]
+        if llm_output == "DOC2":
+          return [
+              data.Extraction(
+                  extraction_class="Person",
+                  extraction_text="Charlie",
+              )
+          ]
+        raise AssertionError(f"Unexpected llm_output: {llm_output!r}")
+
+      def align(
+          self,
+          extractions,
+          chunk_text,
+          token_offset,
+          char_offset,
+          **kwargs,
+      ):
+        return list(extractions)
+
+    annotator = annotation.Annotator(
+        language_model=mock_language_model,
+        prompt_template=prompting.PromptTemplateStructured(description=""),
+    )
+
+    documents = [
+        data.Document(text="Doc1 text", document_id="doc1"),
+        data.Document(text="Doc2 text", document_id="doc2"),
+    ]
+
+    annotations = list(
+        annotator.annotate_documents(
+            documents,
+            resolver=_FakeResolver(),
+            max_char_buffer=200,
+            batch_length=1,
+            debug=False,
+            show_progress=False,
+        )
+    )
+
+    self.assertLen(annotations, 2)
+    self.assertEmpty(call_outputs)
+    self.assertEqual(annotations[0].document_id, "doc1")
+    self.assertEqual(annotations[1].document_id, "doc2")
+    self.assertIsNotNone(annotations[0].extractions)
+    self.assertIsNotNone(annotations[1].extractions)
+    self.assertEqual(
+        [
+            extraction.extraction_text
+            for extraction in annotations[0].extractions
+        ],
+        ["Bob"],
+    )
+    self.assertEqual(
+        [
+            extraction.extraction_text
+            for extraction in annotations[1].extractions
+        ],
+        ["Charlie"],
+    )
+    self.assertIsNot(annotations[0].extractions, annotations[1].extractions)
+
   @parameterized.named_parameters(
       dict(
           testcase_name="same_document_id_contiguous",