diff --git a/surfsense_backend/tests/integration/indexing_pipeline/adapters/test_file_upload_adapter.py b/surfsense_backend/tests/integration/indexing_pipeline/adapters/test_file_upload_adapter.py
index 9c705c1d5..24f2c2cc6 100644
--- a/surfsense_backend/tests/integration/indexing_pipeline/adapters/test_file_upload_adapter.py
+++ b/surfsense_backend/tests/integration/indexing_pipeline/adapters/test_file_upload_adapter.py
@@ -89,7 +89,7 @@ async def test_chunks_written_to_db(db_session, db_search_space, db_user, mocker
 async def test_raises_on_indexing_failure(db_session, db_search_space, db_user, mocker):
     """RuntimeError is raised when the indexing step fails so the caller can fire a failure notification."""
     adapter = UploadDocumentAdapter(db_session)
-    with pytest.raises(RuntimeError):
+    with pytest.raises(RuntimeError, match=r"Embedding failed|Indexing failed"):
         await adapter.index(
             markdown_content="## Hello\n\nSome content.",
             filename="test.pdf",
@@ -106,6 +106,67 @@ async def test_raises_on_indexing_failure(db_session, db_search_space, db_user,
 # ---------------------------------------------------------------------------
 
 
+@pytest.mark.usefixtures(
+    "patched_summarize", "patched_embed_text", "patched_chunk_text"
+)
+async def test_reindex_updates_content(db_session, db_search_space, db_user, mocker):
+    """Document content is updated to the new summary after reindexing."""
+    adapter = UploadDocumentAdapter(db_session)
+    await adapter.index(
+        markdown_content="## Original\n\nOriginal content.",
+        filename="test.pdf",
+        etl_service="UNSTRUCTURED",
+        search_space_id=db_search_space.id,
+        user_id=str(db_user.id),
+        llm=mocker.Mock(),
+    )
+
+    result = await db_session.execute(
+        select(Document).filter(Document.search_space_id == db_search_space.id)
+    )
+    document = result.scalars().first()
+
+    document.source_markdown = "## Edited\n\nNew content after user edit."
+    await db_session.flush()
+
+    await adapter.reindex(document=document, llm=mocker.Mock())
+
+    await db_session.refresh(document)
+    assert document.content == "Mocked summary."
+
+
+@pytest.mark.usefixtures(
+    "patched_summarize", "patched_embed_text", "patched_chunk_text"
+)
+async def test_reindex_updates_content_hash(
+    db_session, db_search_space, db_user, mocker
+):
+    """Content hash is recomputed after reindexing with new source markdown."""
+    adapter = UploadDocumentAdapter(db_session)
+    await adapter.index(
+        markdown_content="## Original\n\nOriginal content.",
+        filename="test.pdf",
+        etl_service="UNSTRUCTURED",
+        search_space_id=db_search_space.id,
+        user_id=str(db_user.id),
+        llm=mocker.Mock(),
+    )
+
+    result = await db_session.execute(
+        select(Document).filter(Document.search_space_id == db_search_space.id)
+    )
+    document = result.scalars().first()
+    original_hash = document.content_hash
+
+    document.source_markdown = "## Edited\n\nNew content after user edit."
+    await db_session.flush()
+
+    await adapter.reindex(document=document, llm=mocker.Mock())
+
+    await db_session.refresh(document)
+    assert document.content_hash != original_hash
+
+
 @pytest.mark.usefixtures(
     "patched_summarize", "patched_embed_text", "patched_chunk_text"
 )
@@ -135,11 +196,14 @@ async def test_reindex_sets_status_ready(db_session, db_search_space, db_user, m
     assert DocumentStatus.is_state(document.status, DocumentStatus.READY)
 
 
-@pytest.mark.usefixtures(
-    "patched_summarize", "patched_embed_text", "patched_chunk_text"
-)
+@pytest.mark.usefixtures("patched_summarize", "patched_embed_text")
 async def test_reindex_replaces_chunks(db_session, db_search_space, db_user, mocker):
-    """Reindexing replaces old chunks rather than appending new ones."""
+    """Reindexing replaces old chunks with new content rather than appending."""
+    mocker.patch(
+        "app.indexing_pipeline.indexing_pipeline_service.chunk_text",
+        side_effect=[["Original chunk."], ["Updated chunk."]],
+    )
+
     adapter = UploadDocumentAdapter(db_session)
     await adapter.index(
         markdown_content="## Original\n\nOriginal content.",
@@ -167,6 +231,7 @@ async def test_reindex_replaces_chunks(db_session, db_search_space, db_user, moc
     chunks = chunks_result.scalars().all()
 
     assert len(chunks) == 1
+    assert chunks[0].content == "Updated chunk."
 
 
 @pytest.mark.usefixtures(
@@ -234,5 +299,30 @@ async def test_reindex_raises_on_failure(
         side_effect=RuntimeError("LLM unavailable"),
     )
 
-    with pytest.raises(RuntimeError):
+    with pytest.raises(RuntimeError, match=r"Embedding failed|Reindexing failed"):
+        await adapter.reindex(document=document, llm=mocker.Mock())
+
+
+async def test_reindex_raises_on_empty_source_markdown(
+    db_session, db_search_space, db_user, mocker
+):
+    """Reindexing a document with no source_markdown raises immediately."""
+    from app.db import DocumentType
+
+    document = Document(
+        title="empty.pdf",
+        document_type=DocumentType.FILE,
+        content="placeholder",
+        content_hash="abc123",
+        unique_identifier_hash="def456",
+        source_markdown="",
+        search_space_id=db_search_space.id,
+        created_by_id=str(db_user.id),
+    )
+    db_session.add(document)
+    await db_session.flush()
+
+    adapter = UploadDocumentAdapter(db_session)
+
+    with pytest.raises(RuntimeError, match="no source_markdown"):
         await adapter.reindex(document=document, llm=mocker.Mock())