diff --git a/flaschengeist/plugins/message_mail.py b/flaschengeist/plugins/message_mail.py
index 978ab0e..ecaa042 100644
--- a/flaschengeist/plugins/message_mail.py
+++ b/flaschengeist/plugins/message_mail.py
@@ -31,7 +31,7 @@ class MailMessagePlugin(Plugin):
             self.send_mail(msg)
 
     def send_mail(self, msg: Message):
-        logger.debug(f"Sending mail to {msg.receiver}")
+        logger.debug(f"Sending mail to {msg.receiver} with subject {msg.subject}")
         if isinstance(msg.receiver, User):
             if not msg.receiver.mail:
                 logger.warning("Could not send Mail, mail missing: {}".format(msg.receiver))
@@ -41,18 +41,12 @@ class MailMessagePlugin(Plugin):
             recipients = userController.get_user_by_role(msg.receiver)
 
         mail = MIMEMultipart()
-        try:
-            mail["From"] = self.mail
-            mail["To"] = ", ".join(recipients)
-        except Exception as e:
-            import traceback
-
-            print(traceback.format_exc())
+        mail["From"] = self.mail
+        mail["To"] = ", ".join(recipients)
         mail["Subject"] = msg.subject
         mail.attach(MIMEText(msg.message))
-        if not hasattr(self, "smtp"):
-            self.__connect()
-        self.smtp.sendmail(self.mail, recipients, mail.as_string())
+        with self.__connect() as smtp:
+            smtp.sendmail(self.mail, recipients, mail.as_string())
 
     def __connect(self):
         if self.crypt == "SSL":
@@ -63,3 +57,4 @@ class MailMessagePlugin(Plugin):
         else:
             raise ValueError("Invalid CRYPT given")
         self.smtp.login(self.user, self.password)
+        return self.smtp