diff --git a/commerce_coordinator/apps/commercetools/serializers.py b/commerce_coordinator/apps/commercetools/serializers.py
index fafac844e..5a3775817 100644
--- a/commerce_coordinator/apps/commercetools/serializers.py
+++ b/commerce_coordinator/apps/commercetools/serializers.py
@@ -87,6 +87,9 @@ class OrderFulfillViewInputSerializer(CoordinatorSerializer):
     line_item_state_id = serializers.CharField(allow_null=False)
     edx_lms_user_id = serializers.IntegerField(allow_null=False)
     message_id = serializers.CharField(allow_null=False)
+    course_title = serializers.CharField(allow_null=False)
+    user_first_name = serializers.CharField(allow_null=False)
+    user_email = serializers.EmailField(allow_null=False)
 
 
 class OrderReturnedViewMessageLineItemReturnItemSerializer(CoordinatorSerializer):
diff --git a/commerce_coordinator/apps/commercetools/sub_messages/tasks.py b/commerce_coordinator/apps/commercetools/sub_messages/tasks.py
index e244ddbd8..bc64c6b13 100644
--- a/commerce_coordinator/apps/commercetools/sub_messages/tasks.py
+++ b/commerce_coordinator/apps/commercetools/sub_messages/tasks.py
@@ -120,7 +120,10 @@ def fulfill_order_placed_message_signal_task(
             'course_mode': get_course_mode_from_ct_order(item),
             'item_quantity': item.quantity,
             'line_item_state_id': line_item_state_id,
-            'message_id': message_id
+            'message_id': message_id,
+            'user_first_name': customer.first_name,
+            'user_email': customer.email,
+            'course_title': item.name.get('en-US', '')
         })
 
         # the following throws and thus doesn't need to be a conditional
diff --git a/commerce_coordinator/apps/commercetools/utils.py b/commerce_coordinator/apps/commercetools/utils.py
index 8f4f6ca60..49a0b239e 100644
--- a/commerce_coordinator/apps/commercetools/utils.py
+++ b/commerce_coordinator/apps/commercetools/utils.py
@@ -65,6 +65,27 @@ def send_order_confirmation_email(
         logger.exception(f"Encountered exception sending Order confirmation email. Exception: {exc}")
 
 
+def send_fulfillment_error_email(
+    lms_user_id, lms_user_email, canvas_entry_properties
+):
+    """ Sends fulfillment error email via Braze. """
+    recipients = [{"external_user_id": lms_user_id, "attributes": {
+        "email": lms_user_email,
+    }}]
+    canvas_id = settings.BRAZE_CT_FULFILLMENT_ERROR_CANVAS_ID
+
+    try:
+        braze_client = get_braze_client()
+        if braze_client:
+            braze_client.send_canvas_message(
+                canvas_id=canvas_id,
+                recipients=recipients,
+                canvas_entry_properties=canvas_entry_properties,
+            )
+    except Exception as exc:  # pylint: disable=broad-exception-caught
+        logger.exception(f"Encountered exception sending Fulfillment Error email. Exception: {exc}")
+
+
 def format_amount_for_braze_canvas(centAmount):
     """
     Utility to convert amount to dollar with 2 decimals percision. Also adds the Dollar signs to resulting value.
diff --git a/commerce_coordinator/apps/lms/signal_handlers.py b/commerce_coordinator/apps/lms/signal_handlers.py
index e9cccfef1..da72e3533 100644
--- a/commerce_coordinator/apps/lms/signal_handlers.py
+++ b/commerce_coordinator/apps/lms/signal_handlers.py
@@ -28,6 +28,9 @@ def fulfill_order_placed_send_enroll_in_course(**kwargs):
         line_item_id=kwargs['line_item_id'],
         item_quantity=kwargs['item_quantity'],
         line_item_state_id=kwargs['line_item_state_id'],
-        message_id=kwargs['message_id']
+        message_id=kwargs['message_id'],
+        user_first_name=kwargs['user_first_name'],
+        user_email=kwargs['user_email'],
+        course_title=kwargs['course_title']
     )
     return async_result.id
diff --git a/commerce_coordinator/apps/lms/tasks.py b/commerce_coordinator/apps/lms/tasks.py
index 5e941fd74..999950c3c 100644
--- a/commerce_coordinator/apps/lms/tasks.py
+++ b/commerce_coordinator/apps/lms/tasks.py
@@ -1,14 +1,16 @@
 """
 LMS Celery tasks
 """
+import json
 
-from celery import shared_task
+from celery import Task, shared_task
 from celery.utils.log import get_task_logger
 from django.contrib.auth import get_user_model
 from requests import RequestException
 
 from commerce_coordinator.apps.commercetools.catalog_info.constants import TwoUKeys
 from commerce_coordinator.apps.commercetools.clients import CommercetoolsAPIClient
+from commerce_coordinator.apps.commercetools.utils import send_fulfillment_error_email
 from commerce_coordinator.apps.lms.clients import LMSAPIClient
 
 # Use the special Celery logger for our tasks
@@ -16,7 +18,48 @@
 User = get_user_model()
 
 
-@shared_task(bind=True, autoretry_for=(RequestException,), retry_kwargs={'max_retries': 5, 'countdown': 3})
+class CourseEnrollTaskAfterReturn(Task):
+    def on_failure(self, exc, task_id, args, kwargs, einfo):
+        error_message = json.loads(exc.response.text).get('message', '')
+        edx_lms_user_id = kwargs.get('edx_lms_user_id')
+        user_email = kwargs.get('user_email')
+        order_number = kwargs.get('order_number')
+        user_first_name = kwargs.get('user_first_name')
+        course_title = kwargs.get('course_title')
+
+        logger.error(
+            f"Task {self.name} failed after max retries with error message: {error_message} "
+            f"for user with User Id: {edx_lms_user_id}, Email: {user_email}, "
+            f"Order Number: {order_number}, Course Title: {course_title}"
+        )
+
+        if (
+            self.request.retries >= self.max_retries
+            and "course mode is expired or otherwise unavailable for course run" in error_message
+        ):
+
+            logger.info(
+                f"Sending Fulfillment Error Email for user with "
+                f"User ID: {edx_lms_user_id}, Email: {user_email}, "
+                f"Order Number: {order_number}, Course Title: {course_title}"
+            )
+
+            canvas_entry_properties = {
+                'order_number': order_number,
+                'product_type': 'course',
+                'product_name': course_title,
+                'first_name': user_first_name,
+            }
+            # Send failure notification email
+            send_fulfillment_error_email(edx_lms_user_id, user_email, canvas_entry_properties)
+
+
+@shared_task(
+    bind=True,
+    autoretry_for=(RequestException,),
+    retry_kwargs={'max_retries': 5, 'countdown': 3},
+    base=CourseEnrollTaskAfterReturn,
+)
 def fulfill_order_placed_send_enroll_in_course_task(
     self,
     course_id,
@@ -32,7 +75,10 @@ def fulfill_order_placed_send_enroll_in_course_task(
     line_item_id,
     item_quantity,
     line_item_state_id,
-    message_id
+    message_id,
+    user_first_name,
+    user_email,
+    course_title
 ):
     """
     Celery task for order placed fulfillment and enrollment via LMS Enrollment API.
diff --git a/commerce_coordinator/settings/base.py b/commerce_coordinator/settings/base.py
index 491d659bc..a51d87cbe 100644
--- a/commerce_coordinator/settings/base.py
+++ b/commerce_coordinator/settings/base.py
@@ -468,6 +468,7 @@ def root(*path_fragments):
 BRAZE_API_KEY = None
 BRAZE_API_SERVER = None
 BRAZE_CT_ORDER_CONFIRMATION_CANVAS_ID = ''
+BRAZE_CT_FULFILLMENT_ERROR_CANVAS_ID = ''
 
 # SEGMENT WRITE KEY
 SEGMENT_KEY = None
diff --git a/commerce_coordinator/settings/local.py b/commerce_coordinator/settings/local.py
index 17bd5c978..6d7803d6e 100644
--- a/commerce_coordinator/settings/local.py
+++ b/commerce_coordinator/settings/local.py
@@ -7,6 +7,7 @@
     'host.docker.internal',
     'localhost',
     '.ngrok-free.app',
+    '.share.zrok.io',
 )
 
 INSTALLED_APPS += (