diff --git a/backend/danswer/background/update.py b/backend/danswer/background/update.py
index 7ed879299296..b3ee6f56fe14 100755
--- a/backend/danswer/background/update.py
+++ b/backend/danswer/background/update.py
@@ -157,8 +157,11 @@ def run_indexing_jobs(db_session: Session) -> None:
                 last_run_time = get_last_successful_attempt_start_time(
                     attempt.connector_id, attempt.credential_id, db_session
                 )
+                # Covers very unlikely case that time offset check from DB having tiny variations that coincide with
+                # a new document being created
+                safe_last_run_time = max(last_run_time - 1, 0.0)
                 doc_batch_generator = runnable_connector.poll_source(
-                    last_run_time, time.time()
+                    safe_last_run_time, time.time()
                 )
 
             else:
diff --git a/backend/danswer/db/engine.py b/backend/danswer/db/engine.py
index 97c4e21c51e8..e5e51287b84c 100644
--- a/backend/danswer/db/engine.py
+++ b/backend/danswer/db/engine.py
@@ -8,6 +8,7 @@ from danswer.configs.app_configs import POSTGRES_HOST
 from danswer.configs.app_configs import POSTGRES_PASSWORD
 from danswer.configs.app_configs import POSTGRES_PORT
 from danswer.configs.app_configs import POSTGRES_USER
+from danswer.utils.logger import setup_logger
 from sqlalchemy import text
 from sqlalchemy.engine import create_engine
 from sqlalchemy.engine import Engine
@@ -16,6 +17,7 @@ from sqlalchemy.ext.asyncio import AsyncSession
 from sqlalchemy.ext.asyncio import create_async_engine
 from sqlalchemy.orm import Session
 
+logger = setup_logger()
 
 SYNC_DB_API = "psycopg2"
 ASYNC_DB_API = "asyncpg"
@@ -28,6 +30,10 @@ _ASYNC_ENGINE: AsyncEngine | None = None
 
 
 def get_db_current_time(db_session: Session) -> datetime:
+    """Get the current time from Postgres representing the start of the transaction
+    Within the same transaction this value will not update
+    This datetime object returned should be timezone aware, default Postgres timezone is UTC
+    """
     result = db_session.execute(text("SELECT NOW()")).scalar()
     if result is None:
         raise ValueError("Database did not return a time")
@@ -37,9 +43,11 @@ def get_db_current_time(db_session: Session) -> datetime:
 def translate_db_time_to_server_time(
     db_time: datetime, db_session: Session
 ) -> datetime:
-    server_now = datetime.now()
+    """If a different database driver is used which does not include timezone info,
+    this should hit an exception rather than being wrong"""
+    server_now = datetime.now(timezone.utc)
     db_now = get_db_current_time(db_session)
-    time_diff = server_now - db_now.astimezone(timezone.utc).replace(tzinfo=None)
+    time_diff = server_now - db_now
     return db_time + time_diff