diff --git a/backend/ee/danswer/db/query_history.py b/backend/ee/danswer/db/query_history.py
index b6a79cb77..8fb77f0a2 100644
--- a/backend/ee/danswer/db/query_history.py
+++ b/backend/ee/danswer/db/query_history.py
@@ -8,6 +8,7 @@ from sqlalchemy import desc
 from sqlalchemy.orm import contains_eager
 from sqlalchemy.orm import joinedload
 from sqlalchemy.orm import Session
+from sqlalchemy.sql.expression import UnaryExpression
 
 from danswer.db.models import ChatMessage
 from danswer.db.models import ChatSession
@@ -20,22 +21,22 @@ def fetch_chat_sessions_eagerly_by_time(
     end: datetime.datetime,
     db_session: Session,
     limit: int | None = 500,
-    initial_id: int | None = None,
+    initial_time: datetime.datetime | None = None,
 ) -> list[ChatSession]:
-    id_order = desc(ChatSession.id)  # type: ignore
-    time_order = desc(ChatSession.time_created)  # type: ignore
-    message_order = asc(ChatMessage.id)  # type: ignore
+    time_order: UnaryExpression = desc(ChatSession.time_created)
+    message_order: UnaryExpression = asc(ChatMessage.id)
 
     filters: list[ColumnElement | BinaryExpression] = [
         ChatSession.time_created.between(start, end)
     ]
 
-    if initial_id:
-        filters.append(ChatSession.id < initial_id)
+    if initial_time:
+        filters.append(ChatSession.time_created > initial_time)
+
     subquery = (
         db_session.query(ChatSession.id, ChatSession.time_created)
         .filter(*filters)
-        .order_by(id_order, time_order)
+        .order_by(ChatSession.id, time_order)
         .distinct(ChatSession.id)
         .limit(limit)
         .subquery()
@@ -43,7 +44,7 @@ def fetch_chat_sessions_eagerly_by_time(
 
     query = (
         db_session.query(ChatSession)
-        .join(subquery, ChatSession.id == subquery.c.id)  # type: ignore
+        .join(subquery, ChatSession.id == subquery.c.id)
         .outerjoin(ChatMessage, ChatSession.id == ChatMessage.chat_session_id)
         .options(
             joinedload(ChatSession.user),
diff --git a/backend/ee/danswer/db/usage_export.py b/backend/ee/danswer/db/usage_export.py
index 6642def13..074e1ae7d 100644
--- a/backend/ee/danswer/db/usage_export.py
+++ b/backend/ee/danswer/db/usage_export.py
@@ -2,6 +2,7 @@ import uuid
 from collections.abc import Generator
 from datetime import datetime
 from typing import IO
+from typing import Optional
 
 from fastapi_users_db_sqlalchemy import UUID_ID
 from sqlalchemy.orm import Session
@@ -19,11 +20,15 @@ from ee.danswer.server.reporting.usage_export_models import UsageReportMetadata
 def get_empty_chat_messages_entries__paginated(
     db_session: Session,
     period: tuple[datetime, datetime],
-    limit: int | None = 1,
-    initial_id: int | None = None,
-) -> list[ChatMessageSkeleton]:
+    limit: int | None = 500,
+    initial_time: datetime | None = None,
+) -> tuple[Optional[datetime], list[ChatMessageSkeleton]]:
     chat_sessions = fetch_chat_sessions_eagerly_by_time(
-        period[0], period[1], db_session, limit=limit, initial_id=initial_id
+        start=period[0],
+        end=period[1],
+        db_session=db_session,
+        limit=limit,
+        initial_time=initial_time,
     )
 
     message_skeletons: list[ChatMessageSkeleton] = []
@@ -36,7 +41,7 @@ def get_empty_chat_messages_entries__paginated(
             flow_type = FlowType.CHAT
 
         for message in chat_session.messages:
-            # only count user messages
+            # Only count user messages
             if message.message_type != MessageType.USER:
                 continue
 
@@ -49,24 +54,34 @@ def get_empty_chat_messages_entries__paginated(
                     time_sent=message.time_sent,
                 )
             )
+    if len(chat_sessions) == 0:
+        return None, []
 
-    return message_skeletons
+    return chat_sessions[0].time_created, message_skeletons
 
 
 def get_all_empty_chat_message_entries(
     db_session: Session,
     period: tuple[datetime, datetime],
 ) -> Generator[list[ChatMessageSkeleton], None, None]:
-    initial_id = None
+    initial_time: Optional[datetime] = period[0]
+    ind = 0
     while True:
-        message_skeletons = get_empty_chat_messages_entries__paginated(
-            db_session, period, initial_id=initial_id
+        ind += 1
+
+        time_created, message_skeletons = get_empty_chat_messages_entries__paginated(
+            db_session,
+            period,
+            initial_time=initial_time,
         )
+
         if not message_skeletons:
             return
 
         yield message_skeletons
-        initial_id = message_skeletons[-1].chat_session_id
+
+        # Update initial_time for the next iteration
+        initial_time = time_created
 
 
 def get_all_usage_reports(db_session: Session) -> list[UsageReportMetadata]: