diff --git a/backend/danswer/background/indexing/checkpointing.py b/backend/danswer/background/indexing/checkpointing.py
index d1d4c8cf4..ec3ce5c8f 100644
--- a/backend/danswer/background/indexing/checkpointing.py
+++ b/backend/danswer/background/indexing/checkpointing.py
@@ -40,8 +40,13 @@ def _default_end_time(
 
 
 def find_end_time_for_indexing_attempt(
-    last_successful_run: datetime.datetime | None, source_type: DocumentSource
+    last_successful_run: datetime.datetime | None,
+    # source_type can be used to override the default for certain connectors, currently unused
+    source_type: DocumentSource,
 ) -> datetime.datetime | None:
+    """Is the current time unless the connector is run over a large period, in which case it is
+    split up into large time segments that become smaller as it approaches the present
+    """
     # NOTE: source_type can be used to override the default for certain connectors
     end_of_window = _default_end_time(last_successful_run)
     now = datetime.datetime.now(tz=datetime.timezone.utc)
diff --git a/backend/danswer/background/update.py b/backend/danswer/background/update.py
index eb1b7943b..20c2c33a2 100755
--- a/backend/danswer/background/update.py
+++ b/backend/danswer/background/update.py
@@ -63,7 +63,9 @@ def _should_create_new_indexing(
     if not last_index:
         return True
 
-    # only one scheduled job per connector at a time
+    # Only one scheduled job per connector at a time
+    # Can schedule another one if the current one is already running however
+    # Because the currently running one will not be until the latest time
     if last_index.status == IndexingStatus.NOT_STARTED:
         return False
 
diff --git a/backend/danswer/db/index_attempt.py b/backend/danswer/db/index_attempt.py
index ed5eac0db..04f3c58a6 100644
--- a/backend/danswer/db/index_attempt.py
+++ b/backend/danswer/db/index_attempt.py
@@ -166,20 +166,24 @@ def get_latest_index_attempts(
 
 
 def get_index_attempts_for_cc_pair(
-    db_session: Session, cc_pair_identifier: ConnectorCredentialPairIdentifier
+    db_session: Session,
+    cc_pair_identifier: ConnectorCredentialPairIdentifier,
+    disinclude_finished: bool = False,
 ) -> Sequence[IndexAttempt]:
-    stmt = (
-        select(IndexAttempt)
-        .where(
-            and_(
-                IndexAttempt.connector_id == cc_pair_identifier.connector_id,
-                IndexAttempt.credential_id == cc_pair_identifier.credential_id,
-            )
-        )
-        .order_by(
-            IndexAttempt.time_created.desc(),
+    stmt = select(IndexAttempt).where(
+        and_(
+            IndexAttempt.connector_id == cc_pair_identifier.connector_id,
+            IndexAttempt.credential_id == cc_pair_identifier.credential_id,
         )
     )
+    if disinclude_finished:
+        stmt = stmt.where(
+            IndexAttempt.status.in_(
+                [IndexingStatus.NOT_STARTED, IndexingStatus.IN_PROGRESS]
+            )
+        )
+
+    stmt = stmt.order_by(IndexAttempt.time_created.desc())
     return db_session.execute(stmt).scalars().all()
 
 
diff --git a/backend/danswer/server/documents/connector.py b/backend/danswer/server/documents/connector.py
index ca3dd325a..28bb8d503 100644
--- a/backend/danswer/server/documents/connector.py
+++ b/backend/danswer/server/documents/connector.py
@@ -56,6 +56,7 @@ from danswer.db.deletion_attempt import check_deletion_attempt_is_allowed
 from danswer.db.document import get_document_cnts_for_cc_pairs
 from danswer.db.engine import get_session
 from danswer.db.index_attempt import create_index_attempt
+from danswer.db.index_attempt import get_index_attempts_for_cc_pair
 from danswer.db.index_attempt import get_latest_index_attempts
 from danswer.db.models import User
 from danswer.dynamic_configs.interface import ConfigNotFoundError
@@ -512,10 +513,31 @@ def connector_run_once(
             detail="Connector has no valid credentials, cannot create index attempts.",
         )
 
+    skipped_credentials = [
+        credential_id
+        for credential_id in credential_ids
+        if get_index_attempts_for_cc_pair(
+            cc_pair_identifier=ConnectorCredentialPairIdentifier(
+                connector_id=run_info.connector_id,
+                credential_id=credential_id,
+            ),
+            disinclude_finished=True,
+            db_session=db_session,
+        )
+    ]
+
     index_attempt_ids = [
         create_index_attempt(run_info.connector_id, credential_id, db_session)
         for credential_id in credential_ids
+        if credential_id not in skipped_credentials
     ]
+
+    if not index_attempt_ids:
+        raise HTTPException(
+            status_code=400,
+            detail="No new indexing attempts created, indexing jobs are queued or running.",
+        )
+
     return StatusResponse(
         success=True,
         message=f"Successfully created {len(index_attempt_ids)} index attempts",