Emails stay in the delivery queue with the message "450 4.4.1 [internal] Connection Timed Out"

Article:TECH146415  |  Created: 2010-12-16  |  Updated: 2010-12-16  |  Article URL
Article Type
Technical Solution


Some or most of email messages are not being delivered properly when using Symantec Brightmail Gateway 8.x or later.




- Under the queue status page you see the message:
"450 4.4.1 [internal] Connection Timed Out"



Symantec Brightmail Gateway 8.x or later



This message indicates that the connection is either timing out or being interrupted while the message is being transferred to its destination which can be a local message or a non-local message.


If you have a firewall between the Symantec Brightmail Gateway appliance and the destination SMTP server which can be a local or non-local mailbox server, make sure SMTP/ESMTP features are disabled.


Please consult with the firewall vendor for information on how to disable these features.


Firewalls that are known to have such features are:


  • Cisco ASA - Disable all esmtp_inspect features
  • Cisco Pix - Disable mailguard
  • Checkpoint - Disable the smart defense technology for SMTP/ESMTP
  • Astaro Firewall - Versions or lower , please check the following link


For other issues that might be caused by these features, please check the following link 


Article URL

Terms of use for this information are found in Legal Notices