diff --git a/app/Listeners/CheckoutableListener.php b/app/Listeners/CheckoutableListener.php
index c5499784b7..6037ee1ec4 100644
--- a/app/Listeners/CheckoutableListener.php
+++ b/app/Listeners/CheckoutableListener.php
@@ -31,6 +31,7 @@ use Illuminate\Support\Facades\Mail;
 use Illuminate\Support\Facades\Notification;
 use Exception;
 use Illuminate\Support\Facades\Log;
+use Illuminate\Support\Str;
 use Osama\LaravelTeamsNotification\TeamsNotification;
 
 class CheckoutableListener
@@ -94,7 +95,7 @@ class CheckoutableListener
 //                 Send Webhook notification
         try{
                 if ($this->shouldSendWebhookNotification()) {
-                    if (Setting::getSettings()->webhook_selected === 'microsoft') {
+                    if ($this->newMicrosoftTeamsWebhookEnabled()) {
                         $message = $this->getCheckoutNotification($event)->toMicrosoftTeams();
                         $notification = new TeamsNotification(Setting::getSettings()->webhook_endpoint);
                         $notification->success()->sendMessage($message[0], $message[1]);  // Send the message to Microsoft Teams
@@ -176,7 +177,7 @@ class CheckoutableListener
         // Send Webhook notification
         try {
             if ($this->shouldSendWebhookNotification()) {
-                    if (Setting::getSettings()->webhook_selected === 'microsoft') {
+                if ($this->newMicrosoftTeamsWebhookEnabled()) {
                         $message = $this->getCheckinNotification($event)->toMicrosoftTeams();
                         $notification = new TeamsNotification(Setting::getSettings()->webhook_endpoint);
                         $notification->success()->sendMessage($message[0], $message[1]);  // Send the message to Microsoft Teams
@@ -345,4 +346,9 @@ class CheckoutableListener
         }
         return (method_exists($event->checkoutable, 'checkin_email') && $event->checkoutable->checkin_email());
     }
+
+    private function newMicrosoftTeamsWebhookEnabled(): bool
+    {
+        return Setting::getSettings()->webhook_selected === 'microsoft' && Str::contains(Setting::getSettings()->webhook_endpoint, 'workflows');
+    }
 }