diff --git a/surfsense_backend/app/agents/chat/multi_agent_chat/shared/middleware/filesystem/backends/kb_postgres.py b/surfsense_backend/app/agents/chat/multi_agent_chat/shared/middleware/filesystem/backends/kb_postgres.py
index 7b8aaf2b0..e13196537 100644
--- a/surfsense_backend/app/agents/chat/multi_agent_chat/shared/middleware/filesystem/backends/kb_postgres.py
+++ b/surfsense_backend/app/agents/chat/multi_agent_chat/shared/middleware/filesystem/backends/kb_postgres.py
@@ -508,7 +508,7 @@ class KBPostgresBackend(BackendProtocol):
             chunk_rows = await session.execute(
                 select(Chunk.id, Chunk.content)
                 .where(Chunk.document_id == document.id)
-                .order_by(Chunk.id)
+                .order_by(Chunk.position, Chunk.id)
             )
             chunks = [
                 {"chunk_id": row.id, "content": row.content} for row in chunk_rows.all()
@@ -725,7 +725,7 @@ class KBPostgresBackend(BackendProtocol):
                         .join(Document, Document.id == Chunk.document_id)
                         .where(Document.search_space_id == self.search_space_id)
                         .where(Chunk.content.ilike(f"%{pattern}%"))
-                        .order_by(Chunk.document_id, Chunk.id)
+                        .order_by(Chunk.document_id, Chunk.position, Chunk.id)
                     )
                     chunk_rows = await session.execute(sub)
                     per_doc: dict[int, int] = {}
diff --git a/surfsense_backend/app/agents/chat/multi_agent_chat/shared/middleware/knowledge_search.py b/surfsense_backend/app/agents/chat/multi_agent_chat/shared/middleware/knowledge_search.py
index 681e80b0e..9ef601791 100644
--- a/surfsense_backend/app/agents/chat/multi_agent_chat/shared/middleware/knowledge_search.py
+++ b/surfsense_backend/app/agents/chat/multi_agent_chat/shared/middleware/knowledge_search.py
@@ -394,7 +394,10 @@ async def browse_recent_documents(
                 Chunk.document_id,
                 Chunk.content,
                 func.row_number()
-                .over(partition_by=Chunk.document_id, order_by=Chunk.id)
+                .over(
+                    partition_by=Chunk.document_id,
+                    order_by=(Chunk.position, Chunk.id),
+                )
                 .label("rn"),
             )
             .where(Chunk.document_id.in_(doc_ids))
@@ -404,7 +407,7 @@ async def browse_recent_documents(
         chunk_query = (
             select(numbered.c.chunk_id, numbered.c.document_id, numbered.c.content)
             .where(numbered.c.rn <= _RECENCY_MAX_CHUNKS_PER_DOC)
-            .order_by(numbered.c.document_id, numbered.c.chunk_id)
+            .order_by(numbered.c.document_id, numbered.c.rn)
         )
         chunk_result = await session.execute(chunk_query)
         fetched_chunks = chunk_result.all()
@@ -531,7 +534,7 @@ async def fetch_mentioned_documents(
         chunk_result = await session.execute(
             select(Chunk.id, Chunk.content, Chunk.document_id)
             .where(Chunk.document_id.in_(list(docs.keys())))
-            .order_by(Chunk.document_id, Chunk.id)
+            .order_by(Chunk.document_id, Chunk.position, Chunk.id)
         )
         chunks_by_doc: dict[int, list[dict[str, Any]]] = {doc_id: [] for doc_id in docs}
         for row in chunk_result.all():
diff --git a/surfsense_backend/app/agents/chat/multi_agent_chat/subagents/builtins/deliverables/tools/knowledge_base.py b/surfsense_backend/app/agents/chat/multi_agent_chat/subagents/builtins/deliverables/tools/knowledge_base.py
index e99e0291a..d89124990 100644
--- a/surfsense_backend/app/agents/chat/multi_agent_chat/subagents/builtins/deliverables/tools/knowledge_base.py
+++ b/surfsense_backend/app/agents/chat/multi_agent_chat/subagents/builtins/deliverables/tools/knowledge_base.py
@@ -122,7 +122,7 @@ async def _browse_recent_documents(
         chunk_query = (
             select(Chunk)
             .where(Chunk.document_id.in_(doc_ids))
-            .order_by(Chunk.document_id, Chunk.id)
+            .order_by(Chunk.document_id, Chunk.position, Chunk.id)
         )
         chunk_result = await session.execute(chunk_query)
         raw_chunks = chunk_result.scalars().all()
diff --git a/surfsense_backend/app/retriever/chunks_hybrid_search.py b/surfsense_backend/app/retriever/chunks_hybrid_search.py
index 47f7fe6b1..5e5edec2e 100644
--- a/surfsense_backend/app/retriever/chunks_hybrid_search.py
+++ b/surfsense_backend/app/retriever/chunks_hybrid_search.py
@@ -420,7 +420,10 @@ class ChucksHybridSearchRetriever:
             select(
                 Chunk.id.label("chunk_id"),
                 func.row_number()
-                .over(partition_by=Chunk.document_id, order_by=Chunk.id)
+                .over(
+                    partition_by=Chunk.document_id,
+                    order_by=(Chunk.position, Chunk.id),
+                )
                 .label("rn"),
             )
             .where(Chunk.document_id.in_(doc_ids))
@@ -441,7 +444,7 @@ class ChucksHybridSearchRetriever:
             select(Chunk.id, Chunk.content, Chunk.document_id)
             .join(numbered, Chunk.id == numbered.c.chunk_id)
             .where(chunk_filter)
-            .order_by(Chunk.document_id, Chunk.id)
+            .order_by(Chunk.document_id, Chunk.position, Chunk.id)
         )
 
         t_fetch = time.perf_counter()
diff --git a/surfsense_backend/app/retriever/documents_hybrid_search.py b/surfsense_backend/app/retriever/documents_hybrid_search.py
index 9ce86d404..d856e93cf 100644
--- a/surfsense_backend/app/retriever/documents_hybrid_search.py
+++ b/surfsense_backend/app/retriever/documents_hybrid_search.py
@@ -357,7 +357,10 @@ class DocumentHybridSearchRetriever:
             select(
                 Chunk.id.label("chunk_id"),
                 func.row_number()
-                .over(partition_by=Chunk.document_id, order_by=Chunk.id)
+                .over(
+                    partition_by=Chunk.document_id,
+                    order_by=(Chunk.position, Chunk.id),
+                )
                 .label("rn"),
             )
             .where(Chunk.document_id.in_(doc_ids))
@@ -369,7 +372,7 @@ class DocumentHybridSearchRetriever:
             select(Chunk.id, Chunk.content, Chunk.document_id)
             .join(numbered, Chunk.id == numbered.c.chunk_id)
             .where(numbered.c.rn <= _MAX_FETCH_CHUNKS_PER_DOC)
-            .order_by(Chunk.document_id, Chunk.id)
+            .order_by(Chunk.document_id, Chunk.position, Chunk.id)
         )
 
         t_fetch = time.perf_counter()
diff --git a/surfsense_backend/app/routes/documents_routes.py b/surfsense_backend/app/routes/documents_routes.py
index 865068fba..53f03a0ca 100644
--- a/surfsense_backend/app/routes/documents_routes.py
+++ b/surfsense_backend/app/routes/documents_routes.py
@@ -1014,8 +1014,8 @@ async def get_document_by_chunk_id(
             .filter(
                 Chunk.document_id == document.id,
                 or_(
-                    Chunk.created_at < chunk.created_at,
-                    and_(Chunk.created_at == chunk.created_at, Chunk.id < chunk.id),
+                    Chunk.position < chunk.position,
+                    and_(Chunk.position == chunk.position, Chunk.id < chunk.id),
                 ),
             )
         )
@@ -1027,7 +1027,7 @@ async def get_document_by_chunk_id(
         windowed_result = await session.execute(
             select(Chunk)
             .filter(Chunk.document_id == document.id)
-            .order_by(Chunk.created_at, Chunk.id)
+            .order_by(Chunk.position, Chunk.id)
             .offset(start)
             .limit(end - start)
         )
@@ -1137,7 +1137,7 @@ async def get_document_chunks_paginated(
         chunks_result = await session.execute(
             select(Chunk)
             .filter(Chunk.document_id == document_id)
-            .order_by(Chunk.created_at, Chunk.id)
+            .order_by(Chunk.position, Chunk.id)
             .offset(offset)
             .limit(page_size)
         )
diff --git a/surfsense_backend/app/routes/editor_routes.py b/surfsense_backend/app/routes/editor_routes.py
index 166164c50..34828964a 100644
--- a/surfsense_backend/app/routes/editor_routes.py
+++ b/surfsense_backend/app/routes/editor_routes.py
@@ -119,7 +119,7 @@ async def get_editor_content(
     chunk_contents_result = await session.execute(
         select(Chunk.content)
         .filter(Chunk.document_id == document_id)
-        .order_by(Chunk.id)
+        .order_by(Chunk.position, Chunk.id)
     )
     chunk_contents = chunk_contents_result.scalars().all()
 
@@ -205,7 +205,7 @@ async def download_document_markdown(
         chunk_contents_result = await session.execute(
             select(Chunk.content)
             .filter(Chunk.document_id == document_id)
-            .order_by(Chunk.id)
+            .order_by(Chunk.position, Chunk.id)
         )
         chunk_contents = chunk_contents_result.scalars().all()
         if chunk_contents:
@@ -354,7 +354,7 @@ async def export_document(
         chunk_contents_result = await session.execute(
             select(Chunk.content)
             .filter(Chunk.document_id == document_id)
-            .order_by(Chunk.id)
+            .order_by(Chunk.position, Chunk.id)
         )
         chunk_contents = chunk_contents_result.scalars().all()
         if chunk_contents:
diff --git a/surfsense_backend/app/services/ai_file_sort_service.py b/surfsense_backend/app/services/ai_file_sort_service.py
index 2f04131a6..1bf4d325e 100644
--- a/surfsense_backend/app/services/ai_file_sort_service.py
+++ b/surfsense_backend/app/services/ai_file_sort_service.py
@@ -156,7 +156,7 @@ async def _resolve_document_text(
     stmt = (
         select(Chunk.content)
         .where(Chunk.document_id == document.id)
-        .order_by(Chunk.id)
+        .order_by(Chunk.position, Chunk.id)
         .limit(_MAX_CHUNKS_FOR_CONTEXT)
     )
     result = await session.execute(stmt)
diff --git a/surfsense_backend/app/services/export_service.py b/surfsense_backend/app/services/export_service.py
index 97f952223..9e6869fe1 100644
--- a/surfsense_backend/app/services/export_service.py
+++ b/surfsense_backend/app/services/export_service.py
@@ -62,7 +62,7 @@ async def _get_document_markdown(
     chunk_result = await session.execute(
         select(Chunk.content)
         .filter(Chunk.document_id == document.id)
-        .order_by(Chunk.id)
+        .order_by(Chunk.position, Chunk.id)
     )
     chunks = chunk_result.scalars().all()
     if chunks: