diff --git a/aws/eks/cloudwatch_alarms.tf b/aws/eks/cloudwatch_alarms.tf
index dd847131e..4daf6e5da 100644
--- a/aws/eks/cloudwatch_alarms.tf
+++ b/aws/eks/cloudwatch_alarms.tf
@@ -958,14 +958,29 @@ resource "aws_cloudwatch_metric_alarm" "github-arc-runner-error-alarm" {
 resource "aws_cloudwatch_metric_alarm" "service-callback-too-many-failures-warning" {
   count               = var.cloudwatch_enabled ? 1 : 0
   alarm_name          = "service-callback-too-many-failures-warning"
-  alarm_description   = "Service reached the max number of callback retries 5 times in 30 minutes"
+  alarm_description   = "Service reached the max number of callback retries 25 times in 5 minutes"
   comparison_operator = "GreaterThanOrEqualToThreshold"
   evaluation_periods  = "1"
-  metric_name         = aws_cloudwatch_log_metric_filter.callback-max-retry-failures[0].metric_transformation[0].name
-  namespace           = aws_cloudwatch_log_metric_filter.callback-max-retry-failures[0].metric_transformation[0].namespace
-  period              = 60 * 30
+  metric_name         = aws_cloudwatch_log_metric_filter.callback-request-failures[0].metric_transformation[0].name
+  namespace           = aws_cloudwatch_log_metric_filter.callback-request-failures[0].metric_transformation[0].namespace
+  period              = 60 * 5
   statistic           = "Sum"
-  threshold           = 5
+  threshold           = 25
   treat_missing_data  = "notBreaching"
   alarm_actions       = [var.sns_alert_warning_arn]
 }
+
+resource "aws_cloudwatch_metric_alarm" "service-callback-too-many-failures-critical" {
+  count               = var.cloudwatch_enabled ? 1 : 0
+  alarm_name          = "service-callback-too-many-failures-warning"
+  alarm_description   = "Service reached the max number of callback retries 100 times in 10 minutes"
+  comparison_operator = "GreaterThanOrEqualToThreshold"
+  evaluation_periods  = "1"
+  metric_name         = aws_cloudwatch_log_metric_filter.callback-request-failures[0].metric_transformation[0].name
+  namespace           = aws_cloudwatch_log_metric_filter.callback-request-failures[0].metric_transformation[0].namespace
+  period              = 60 * 10
+  statistic           = "Sum"
+  threshold           = 100
+  treat_missing_data  = "notBreaching"
+  alarm_actions       = [var.sns_alert_critical_arn]
+}
diff --git a/aws/eks/cloudwatch_log.tf b/aws/eks/cloudwatch_log.tf
index fed7d25d1..cfe8275e9 100644
--- a/aws/eks/cloudwatch_log.tf
+++ b/aws/eks/cloudwatch_log.tf
@@ -180,10 +180,10 @@ resource "aws_cloudwatch_log_metric_filter" "github-arc-runner-alarm" {
   }
 }
 
-resource "aws_cloudwatch_log_metric_filter" "callback-max-retry-failures" {
+resource "aws_cloudwatch_log_metric_filter" "callback-request-failures" {
   count          = var.cloudwatch_enabled ? 1 : 0
-  name           = "callback-max-retry-failures"
-  pattern        = "send_delivery_status_to_service has retried the max num of times for callback url"
+  name           = "callback-request-failures"
+  pattern        = "send_delivery_status_to_service request failed for notification_id:"
   log_group_name = aws_cloudwatch_log_group.notification-canada-ca-eks-application-logs[0].name
 
   metric_transformation {
diff --git a/aws/eks/cloudwatch_queries.tf b/aws/eks/cloudwatch_queries.tf
index 03cf8a866..f743b4470 100644
--- a/aws/eks/cloudwatch_queries.tf
+++ b/aws/eks/cloudwatch_queries.tf
@@ -272,9 +272,9 @@ fields @timestamp, @service_id, @bounce_type
 QUERY
 }
 
-resource "aws_cloudwatch_query_definition" "callback-failures-by-service" {
+resource "aws_cloudwatch_query_definition" "callback-max-retry-failures-by-service" {
   count = var.cloudwatch_enabled ? 1 : 0
-  name  = "Callbacks / Count of callbacks that exceeded MaxRetries by service"
+  name  = "Callbacks / Callbacks that exceeded MaxRetries by service"
 
   log_group_names = [
     local.eks_application_log_group
@@ -291,6 +291,23 @@ fields @timestamp, @service_id, @callback_url, @notification_id
 QUERY
 }
 
+resource "aws_cloudwatch_query_definition" "callback-failures" {
+  count = var.cloudwatch_enabled ? 1 : 0
+  name  = "Callbacks / Callback errors by notification_id"
+
+  log_group_names = [
+    local.eks_application_log_group
+  ]
+
+  query_string = <<QUERY
+fields @timestamp, @notification_id, @url, @error
+| filter kubernetes.container_name like /^celery/
+| filter @message like /send_delivery_status_to_service request failed for notification_id:/
+| parse @message 'send_delivery_status_to_service request failed for notification_id: * and url: * exc: *' as @notification_id, @url, @error
+| limit 10000
+QUERY
+}
+
 resource "aws_cloudwatch_query_definition" "gh-arc-errors" {
   count = var.cloudwatch_enabled ? 1 : 0
   name  = "CICD / GitHub ARC Errors"