diff --git a/backend/danswer/connectors/cross_connector_utils/miscellaneous_utils.py b/backend/danswer/connectors/cross_connector_utils/miscellaneous_utils.py
index 1b79c4a4faf..8e8ea8d7d65 100644
--- a/backend/danswer/connectors/cross_connector_utils/miscellaneous_utils.py
+++ b/backend/danswer/connectors/cross_connector_utils/miscellaneous_utils.py
@@ -23,7 +23,16 @@ def datetime_to_utc(dt: datetime) -> datetime:
 
 
 def time_str_to_utc(datetime_str: str) -> datetime:
-    dt = parse(datetime_str)
+    try:
+        dt = parse(datetime_str)
+    except ValueError:
+        # Handle malformed timezone by attempting to fix common format issues
+        if "0000" in datetime_str:
+            # Convert "0000" to "+0000" for proper timezone parsing
+            fixed_dt_str = datetime_str.replace(" 0000", " +0000")
+            dt = parse(fixed_dt_str)
+        else:
+            raise
     return datetime_to_utc(dt)
 
 
diff --git a/backend/danswer/connectors/gmail/connector.py b/backend/danswer/connectors/gmail/connector.py
index 42d2f305f73..376f03e71d0 100644
--- a/backend/danswer/connectors/gmail/connector.py
+++ b/backend/danswer/connectors/gmail/connector.py
@@ -1,4 +1,8 @@
+import re
+import time
 from base64 import urlsafe_b64decode
+from datetime import datetime
+from datetime import timezone
 from typing import Any
 from typing import cast
 from typing import Dict
@@ -6,6 +10,7 @@
 from google.oauth2.credentials import Credentials as OAuthCredentials  # type: ignore
 from google.oauth2.service_account import Credentials as ServiceAccountCredentials  # type: ignore
 from googleapiclient import discovery  # type: ignore
+from googleapiclient.errors import HttpError  # type: ignore
 
 from danswer.configs.app_configs import INDEX_BATCH_SIZE
 from danswer.configs.constants import DocumentSource
@@ -34,6 +39,64 @@
 logger = setup_logger()
 
 
+def _execute_with_retry(request: Any) -> Any:
+    max_attempts = 10
+    attempt = 0
+
+    while attempt < max_attempts:
+        # Note for reasons unknown, the Google API will sometimes return a 429
+        # and even after waiting the retry period, it will return another 429.
+        # It could be due to a few possibilities:
+        # 1. Other things are also requesting from the Gmail API with the same key
+        # 2. It's a rolling rate limit so the moment we get some amount of requests cleared, we hit it again very quickly
+        # 3. The retry-after has a maximum and we've already hit the limit for the day
+        # or it's something else...
+        try:
+            return request.execute()
+        except HttpError as error:
+            attempt += 1
+
+            if error.resp.status == 429:
+                # Attempt to get 'Retry-After' from headers
+                retry_after = error.resp.get("Retry-After")
+                if retry_after:
+                    sleep_time = int(retry_after)
+                else:
+                    # Extract 'Retry after' timestamp from error message
+                    match = re.search(
+                        r"Retry after (\d{4}-\d{2}-\d{2}T\d{2}:\d{2}:\d{2}\.\d+Z)",
+                        str(error),
+                    )
+                    if match:
+                        retry_after_timestamp = match.group(1)
+                        retry_after_dt = datetime.strptime(
+                            retry_after_timestamp, "%Y-%m-%dT%H:%M:%S.%fZ"
+                        ).replace(tzinfo=timezone.utc)
+                        current_time = datetime.now(timezone.utc)
+                        sleep_time = max(
+                            int((retry_after_dt - current_time).total_seconds()),
+                            0,
+                        )
+                    else:
+                        logger.error(
+                            f"No Retry-After header or timestamp found in error message: {error}"
+                        )
+                        sleep_time = 60
+
+                sleep_time += 3  # Add a buffer to be safe
+
+                logger.info(
+                    f"Rate limit exceeded. Attempt {attempt}/{max_attempts}. Sleeping for {sleep_time} seconds."
+                )
+                time.sleep(sleep_time)
+
+            else:
+                raise
+
+    # If we've exhausted all attempts
+    raise Exception(f"Failed to execute request after {max_attempts} attempts")
+
+
 class GmailConnector(LoadConnector, PollConnector):
     def __init__(self, batch_size: int = INDEX_BATCH_SIZE) -> None:
         self.batch_size = batch_size
@@ -156,7 +219,7 @@ def _fetch_mails_from_gmail(
         query = GmailConnector._build_time_range_query(time_range_start, time_range_end)
         service = discovery.build("gmail", "v1", credentials=self.creds)
         while page_token is not None:
-            result = (
+            result = _execute_with_retry(
                 service.users()
                 .messages()
                 .list(
@@ -165,18 +228,17 @@ def _fetch_mails_from_gmail(
                     q=query,
                     maxResults=self.batch_size,
                 )
-                .execute()
             )
+
             page_token = result.get("nextPageToken")
             messages = result.get("messages", [])
             doc_batch = []
             for message in messages:
                 message_id = message["id"]
-                msg = (
+                msg = _execute_with_retry(
                     service.users()
                     .messages()
                     .get(userId="me", id=message_id, format="full")
-                    .execute()
                 )
                 doc = self._email_to_document(msg)
                 doc_batch.append(doc)